BURIED TREASURES: CASCADES WE HAVEN'T SEEN
|
|
|
- Bartholomew Strickland
- 5 years ago
- Views:
Transcription
1 BURIED TREASURES: CASCADES WE AVE'T SEE Me Me Me 2 3 C C 3 3 C C 3 C 2 Me R. Robinson, J. Chem. Soc., 1917, 762
2 Cascades Articulated Main Entry: 1cas cade Pronunciation: (")kas-'kad Function: noun Etymology: French, from Italian cascata, from cascare to fall, from (assumed) Vulgar Latin casicare, from Latin casus fall, Date: : a steep usually small fall of water; especially :one of a series 2a : something arranged or occurring in a series or in a succession of stages so that each stage derives from or acts upon the product of the preceding <blood clotting involves a biochemical cascade > b: a fall of material (as lace) that hangs in a zigzag line 3: something falling or rushing forth in quantity <a cascade of sound> <a cascade of events> 4: ne-pot, sequential reactions involving more than one intermediate, preferrably 1) leading to an increase in molecular complexity and 2) without changing reaction conditions see: Chem. Commun., 2003, 551
3 Cascades Articulated Main Entry: 1cas cade Pronunciation: (")kas-'kad Function: noun Etymology: French, from Italian cascata, from cascare to fall, from (assumed) Vulgar Latin casicare, from Latin casus fall, Date: : a steep usually small fall of water; especially :one of a series 2a : something arranged or occurring in a series or in a succession of stages so that each stage derives from or acts upon the product of the preceding <blood clotting involves a biochemical cascade > b: a fall of material (as lace) that hangs in a zigzag line 3: something falling or rushing forth in quantity <a cascade of sound> <a cascade of events> 4: ne-pot, sequential reactions involving more than one intermediate, preferrably 1) leading to an increase in molecular complexity and 2) without changing reaction conditions see: Chem. Commun., 2003, 551
4 Some Inspiration C 2 Me icolaou, K. C., J. Amer. Chem. Soc., 1982, ) 2, Pd/BaS 4 quinoline 2) toluene, 100 C 3 intermediates C 2 Me Me Me Me, TFA, 1,2-dichloroethane; Me Me Me K 2 C 3, 2, Me Johnson, W. S., J. Amer. Chem. Soc., 1971, intermediates Me 3 C P P R C 3 P Sorensen, E. J., J. Amer. Chem. Soc., 2002, 4552 Se mcpba, C 2 Cl 2 ; 40 C, CCl 3 4 intermediates P 1 3 C 3 C R P 1 P 2 C 3 C 3
5 Some Inspiration C 2 Me icolaou, K. C., J. Amer. Chem. Soc., 1982, ) 2, Pd/BaS 4 quinoline 2) toluene, 100 C 3 intermediates C 2 Me Me Me Me, TFA, 1,2-dichloroethane; Me Me Me K 2 C 3, 2, Me Johnson, W. S., J. Amer. Chem. Soc., 1971, intermediates Me 3 C P P R C 3 P Sorensen, E. J., J. Amer. Chem. Soc., 2002, 4552 Se mcpba, C 2 Cl 2 ; 40 C, CCl 3 4 intermediates P 1 3 C 3 C R P 1 P 2 C 3 C 3
6 Some Inspiration C 2 Me icolaou, K. C., J. Amer. Chem. Soc., 1982, ) 2, Pd/BaS 4 quinoline 2) toluene, 100 C 3 intermediates C 2 Me Me Me Me, TFA, 1,2-dichloroethane; Me Me Me K 2 C 3, 2, Me Johnson, W. S., J. Amer. Chem. Soc., 1971, intermediates Me 3 C P P R C 3 P Sorensen, E. J., J. Amer. Chem. Soc., 2002, 4552 Se mcpba, C 2 Cl 2 ; 40 C, CCl 3 4 intermediates P 1 3 C 3 C R P 1 P 2 C 3 C 3
7 Dihydropyridone Synthesis Chem. arm. Bull., 1987, 4730 Et, hu Et Me 2 C -C Me 2 C Me 2 C Me 2 C
8 Dihydropyridone Synthesis Chem. arm. Bull., 1987, 4730 Et, hu Et Me 2 C -C Me 2 C Me 2 C Me 2 C
9 Dihydropyridone Synthesis Chem. arm. Bull., 1987, 4730 Et, hu Et Me 2 C -C Me 2 C Me 2 C Me 2 C
10 Dihydropyridone Synthesis Chem. arm. Bull., 1987, 4730 Et, hu Et Me 2 C -C Me 2 C Me 2 C Me 2 C
11 Dihydropyridone Synthesis Chem. arm. Bull., 1987, 4730 Et, hu Et Me 2 C -C Me 2 C Me 2 C Me 2 C
12 Dihydropyridone Synthesis Chem. arm. Bull., 1987, 4730 Et, hu Et Me 2 C -C Me 2 C Me 2 C Me 2 C
13 Degredation to a Cyclohexadiene Angew. Chem. Int. Ed., 1975, 765. C 3 Li Et 2 C 3 Li
14 Degredation to a Cyclohexadiene Angew. Chem. Int. Ed., 1975, 765. C 3 Li Et 2 C 3 Li
15 Degredation to a Cyclohexadiene Angew. Chem. Int. Ed., 1975, 765. C 3 Li Et 2 C 3 Li
16 Degredation to a Cyclohexadiene Angew. Chem. Int. Ed., 1975, 765. C 3 Li Et 2 C 3 Li
17 Degredation to a Cyclohexadiene Angew. Chem. Int. Ed., 1975, 765. C 3 Li Et 2 C 3 Li
18 C 2 I 2, Zn/Cu Starting Material? Angew. Chem. Intern. Ed., 1975, C 2 I 2, Zn/Cu 2. C 3 3. MeLi, Et 2 C 3, KtBu MeLi Li Et 2
19 C 2 I 2, Zn/Cu Starting Material? Angew. Chem. Intern. Ed., 1975, C 2 I 2, Zn/Cu 2. C 3 3. MeLi, Et 2 C 3, KtBu MeLi Li Et 2
20 C 2 I 2, Zn/Cu Starting Material? Angew. Chem. Intern. Ed., 1975, C 2 I 2, Zn/Cu 2. C 3 3. MeLi, Et 2 C 3, KtBu MeLi Li Et 2
21 C 2 I 2, Zn/Cu Starting Material? Angew. Chem. Intern. Ed., 1975, C 2 I 2, Zn/Cu 2. C 3 3. MeLi, Et 2 C 3, KtBu MeLi Li Et 2
22 C 2 I 2, Zn/Cu Starting Material? Angew. Chem. Intern. Ed., 1975, C 2 I 2, Zn/Cu 2. C 3 3. MeLi, Et 2 C 3, KtBu MeLi Li Et 2
23 Synthesis of a Tetrayne Tetrahedron Lett., 1976, 2663 Ac BuLi; CuCl BuLi Cu + Ac Li Cu + Ac Cu Symmetry Forbidden
24 Synthesis of a Tetrayne Tetrahedron Lett., 1976, 2663 Ac BuLi; CuCl BuLi Cu + Ac Li Cu + Ac Cu Symmetry Forbidden
25 Synthesis of a Tetrayne Tetrahedron Lett., 1976, 2663 Ac BuLi; CuCl BuLi Cu + Ac Li Cu + Ac Cu Symmetry Forbidden
26 Synthesis of a Tetrayne Tetrahedron Lett., 1976, 2663 Ac BuLi; CuCl BuLi Cu + Ac Li Cu + Ac Cu Symmetry Forbidden
27 Synthesis of a Tetrayne Tetrahedron Lett., 1976, 2663 Ac BuLi; CuCl BuLi Cu + Ac Li Cu + Ac Cu Symmetry Forbidden
28 Complex Polycycle J. Am. Chem. Soc., 2001, Bu 3 Sn SnBu 3 Pd(P 3 ) 4, D xidative Addition PdL n Migratory Insertion PdL n Transmetallation Bu 3 Sn SnBu 3 SnBu 3
29 Complex Polycycle J. Am. Chem. Soc., 2001, Bu 3 Sn SnBu 3 Pd(P 3 ) 4, D xidative Addition PdL n Migratory Insertion PdL n Transmetallation Bu 3 Sn SnBu 3 SnBu 3
30 Complex Polycycle J. Am. Chem. Soc., 2001, Bu 3 Sn SnBu 3 Pd(P 3 ) 4, D xidative Addition PdL n Migratory Insertion PdL n Transmetallation Bu 3 Sn SnBu 3 SnBu 3
31 Complex Polycycle J. Am. Chem. Soc., 2001, Bu 3 Sn SnBu 3 Pd(P 3 ) 4, D xidative Addition PdL n Migratory Insertion PdL n Transmetallation Bu 3 Sn SnBu 3 SnBu 3
32 Complex Polycycle Cont... J. Am. Chem. Soc., 2001, e- disrotatory - SnBu 3 SnBu 3 1 transfer -
33 Complex Polycycle Cont... J. Am. Chem. Soc., 2001, e- disrotatory - SnBu 3 SnBu 3 1 transfer -
34 A [3.2.0] Bicycle J. rg. Chem., 1994, 8092 Me 2 C TBDPS Si I TMSI, (TMS) 2 TBDPS I TMS C 2 Me TMS 2 TBDPS I - TMS C 2 Me TBDPS I Me TMS + TBDPS I C 2 Me TMS
35 A [3.2.0] Bicycle J. rg. Chem., 1994, 8092 Me 2 C TBDPS Si I TMSI, (TMS) 2 TBDPS I TMS C 2 Me TMS 2 TBDPS I - TMS C 2 Me TBDPS I Me TMS + TBDPS I C 2 Me TMS
36 A [3.2.0] Bicycle J. rg. Chem., 1994, 8092 Me 2 C TBDPS Si I TMSI, (TMS) 2 TBDPS I TMS C 2 Me TMS 2 TBDPS I - TMS C 2 Me TBDPS I Me TMS + TBDPS I C 2 Me TMS
37 A [3.2.0] Bicycle J. rg. Chem., 1994, 8092 Me 2 C TBDPS Si I TMSI, (TMS) 2 TBDPS I TMS C 2 Me TMS 2 TBDPS I - TMS C 2 Me TBDPS I Me TMS + TBDPS I C 2 Me TMS
38 A [3.2.0] Bicycle J. rg. Chem., 1994, 8092 Me 2 C TBDPS Si I TMSI, (TMS) 2 TBDPS I TMS C 2 Me TMS 2 TBDPS I - TMS C 2 Me TBDPS I Me TMS + TBDPS I C 2 Me TMS
39 A [3.2.0] Bicycle J. rg. Chem., 1994, 8092 Me 2 C TBDPS Si I TMSI, (TMS) 2 TBDPS I TMS C 2 Me TMS 2 TBDPS I - TMS C 2 Me TBDPS I Me TMS + TBDPS I C 2 Me TMS
40 A ydrindane Unpublished P 3, D P 3 P() 3
41 A ydrindane Unpublished P 3, D P 3 P() 3
42 A ydrindane Unpublished P 3, D P 3 P() 3
43 Another (the same) ydrindane oye, T., Unpublished Bn Grubbs Bn Bn Bn Bn Bn Bn
44 Another (the same) ydrindane oye, T., Unpublished Bn Grubbs Bn Bn Bn Bn Bn Bn
45 Another (the same) ydrindane oye, T., Unpublished Bn Grubbs Bn Bn Bn Bn Bn Bn
46 Summary Et, hu Et Me 2 C TBDPS TMSI (TMS) 2 I TBDPS TMS C 2 Me C 3 Li MeLi, Et 2 Et 2 Ac BuLi; CuCl P 3, D Bu 3 Sn SnBu 3 Bn Grubbs Bn Pd(P 3 ) 4, D
A Stereoselective Synthesis of (+)-Gonyautoxin 3
A Stereoselective Synthesis of (+)-Gonyautoxin 3 Mulcahy, J. V.; Du Bois, J. J. Am. Chem. Soc. 2008, 130, 12630-12631 Total Synthesis of (+)-Lithospermic Acid by Asymmetric Intramolecular Alkylation via
Total Synthesis of Oxazolomycin A
Total Synthesis of xazolomycin A Me xazolomycin A Me Eto, K.; Yoshino, M.; Takahashi K.; Ishihara, J.; atakeyama S. rg. Lett. 2011, 13, 5398 Dimas Paz Wipf group- Current Literature ctober 8, 2011 Dimas
Total Synthesis towards Maoecrystal V
Total Synthesis towards Maoecrystal V isolated from the leaves of a Chinese medicinal herb, Isodon eriocalyx in 2004. structure was determined by comprehensive NMR and MS spectroscopic analysis and confirmed
Rhenium-Catalyzed Synthesis of Multisubstituted Aromatic Compounds via C-C Single-Bond Cleavage
henium-catalyzed Synthesis of Multisubstituted Aromatic Compounds via C-C Single-Bond Cleavage Kuninobu, Y.; Takata,.; Kawata, A.; Takai, K. rg. Lett. ASAP Et 5 6 cat. [ebr(c) 3 (thf)] 2 5 6 Current Literature
Studies toward the Synthesis of Azadirachtin: Total Synthesis of a Fully Functionalized ABC Framework and Coupling with a Norbornene Domain
Studies toward the Synthesis of Azadirachtin: Total Synthesis of a Fully Functionalized ABC Framework and Coupling with a Norbornene Domain Nicolaou and Co-workers Angew. Chem. Int. Ed. 2005, 44, 3443
VI. Metal alkyls from oxidative addition / insertion
V. Metal alkyls from oxidative addition / insertion A. Carbonylation - C insertion very facile, metal acyls easily cleaved, all substrates which undergo oxidative addition can in principle be carbonylated.
Additions to Metal-Alkene and -Alkyne Complexes
Additions to tal-alkene and -Alkyne Complexes ecal that alkenes, alkynes and other π-systems can be excellent ligands for transition metals. As a consequence of this binding, the nature of the π-system
transmetallate displace ox. add. M + (insert) (β-elim.)
Chapter IV. Transition Metal σ-alkyl Complexes I. General For much of the rest of this course it will be necessary to understand how σ-alkyl metal complexes are formed and how they react. This is summarized
Electrophilic Carbenes
Electrophilic Carbenes The reaction of so-called stabilized diazo compounds with late transition metals produces a metal carbene intermediate that is electrophilic. The most common catalysts are Cu(I)
Highlights of Schmidt Reaction in the Last Ten Years
ighlights of Schmidt eaction in the Last Ten Years Dendrobates histrionicus Jack Liu ov. 18, 2003 Introduction Classical Schmidt reaction of aldehydes and carboxylic acids Classical Schmidt reaction of
Domino Reactions in Total Synthesis! Reporter: Tianhe Yang! Supervisors: Prof. Yang! Prof. Chen! Prof. Tang!
1! Domino Reactions in Total Synthesis! Reporter: Tianhe Yang! Supervisors: Prof. Yang! Prof. Chen! Prof. Tang! 2! utline! 1. Brief Introduction! 2. ucleophilic Dominoes! 3. Electrophilc Dominoes! 4. Radical
Towards Maoecrystal V: A Comparison of Recent Strategies
Towards Maoecrystal V: A Comparison of Recent Strategies Reactant/Reagent Current Literature: November 14, 2009 lissa Sprachman lissa Sprachman @ Wipf Group Page 1 of 14 12/28/2009 Maoecrystal V: Structural
o-palladated cat. [Chem. Comm (1999)] [Org. Lett. 2, 1826 (2000)] [Org. Lett. 2, 2881 (2000)] [JACS 41, 9550 (1999)]
![o-palladated cat. [Chem. Comm (1999)] [Org. Lett. 2, 1826 (2000)] [Org. Lett. 2, 2881 (2000)] [JACS 41, 9550 (1999)]](/thumbs/85/92754396.jpg "o-palladated cat. [Chem. Comm (1999)] [Org. Lett. 2, 1826 (2000)] [Org. Lett. 2, 2881 (2000)] [JACS 41, 9550 (1999)]")
3. Boron -- eview [Suzuki Chem. ev. 95, 2457 (1995)] U77b ydroboration also attractive but B Pd transmetallation difficult - must produce stable B product - solved (by Suzuki) by adding base to make Borates
O OH N. Me OMe N NH HO H Debenzoyltashironin NMe 2. Phalarine. Anne-Marie Dechert
Recent ighlights ht from the Danishefsky Laboratory 11-0-Debenzoyltashironin 2 Phalarine Anne-Marie Dechert ovember 7, 2007 11-0-Debenzoyltashironin Background and Structural Features Isolated from the
Highlights in the Progress of Biomimetic Strategies for the Construction of Complex Natural Products. Chris Galliford 26 th August 2003
ighlights in the Progress of Biomimetic Strategies for the Construction of Complex Natural Products Chris Galliford 26 th August 2003 The Biomimetic Approach Inspiration for biomimetic synthesis of a target
Synthesis of Resorcinylic Macrolides
Synthesis of Resorcinylic Macrolides X H H H H Cl X= Radicicol (1) X= CH2 Cycloproparadicicol (2) Danishefsky, S. J. J. Am. Chem. Soc. 2004, 126, ASAP Danishefsky, S. J. rg. Lett. 2004, 6, 413-416 Danishefsky,
Carbonyl Ylide Cycloadditions
Carbonyl Ylide Cycloadditions cond. icholas Anderson Denmark Group eting 07/13/10 Carbonyl Ylides Uncharged 1,3-Dipole Conjugated π-system ighly reactive on-isolable Generate in-situ Carbonyl Ylide Stability
Total Synthesis of the Proposed Structure of Briarellin J
Total Synthesis of the Proposed Structure of Briarellin J Michael T. Crimmins, Mark C. Mans, and Abimael D. Rodríguez. rg. Lett. 2010, ASAP Ac Ac originally proposed structure revised structure Eric E.
11-Step Enantioselective Synthesis of ( )-Lomaiviticin Aglycon
11-Step Enantioselective Synthesis of ( )-Lomaiviticin Aglycon Seth B. erzon, Liang Lu, Christina M. Woo, and Shivajirao L. Gholap J. Am. Chem. Soc. ASAP DI 10.1021/ja200034b Melissa Sprachman Current
Total Syntheses of Minfiensine
Total Syntheses of Minfiensine Douany, A. B.; umphreys, P. G.; verman, L. E.*; Wrobelski, A. D., J. Am. Chem. Soc. 2008, ASAP. D: 10.1021/ja800163v Shen, L.; Zhang, M.; Wu, Y.; Qin, Y.*, Angew. Chem. nt.
A Tandem Semipinacol Rearrangement/Alkylation of a-epoxy Alcohols: An Efficient and Stereoselective Approach to Multifunctional 1,3-Diols
A Tandem Semipinacol Rearrangement/Alkylation of a-epoxy Alcohols: An Efficient and Stereoselective Approach to Multifunctional 1,3-Diols B() 2 H H B() 2 H H Hu, X.-D.; Fan, C.-A.; Zhang, F.-M.; Tu, Y.
Recent Development in. Tandem Radical Reactions (TRR)
ecent Development in Tandem adical eactions (T) Feng u Jan. 13, 2006 Contents Brief Introduction of the istory of T Definition of T Intramolecular T Intermolecular T T as Key Steps in Total Synthesis of
Direct Oxidative Heck Cyclizations: Intramolecular Fujiwara-Moritani Arylations for the Synthesis of Functionalized Benzofurans and Dihydrobenzofurans
Direct xidative eck Cyclizations: Intramolecular Fujiwara-Moritani Arylations for the Synthesis of Functionalized Benzofurans and Dihydrobenzofurans by Zhang,.; Ferreira, E. M.; Stoltz, B. M. Angewandte
Chiral Diol Promoted Boronates Addi3on Reac3ons. Lu Yan Morken Group Boston College
Chiral Diol Promoted Boronates Addi3on Reac3ons Lu Yan Morken Group Boston College Main Idea R R B or R R B Ar * exchange B * * or B Ar R 1 R 1 R 2 R 1 R 2 Products not nucleophilic enough nucleophilic
Mild Cobalt-Catalyzed Hydrocyanation of Olefins with Tosyl Cyanide
Mild Cobalt-Catalyzed ydrocyanation of lefins with Tosyl Cyanide 1 3 2 + Ts Co cat., Si 3 Et, 1-3 h, T 1 2 3 Gaspar, B.; Carreira, E. M. Angew. Chem. Int. Ed. ASAP Current Literature Kalyani Patil 12 May
Palladium-Catalyzed Oxygenation of Unactivated sp 3 C-H Bonds
Palladium-Catalyzed xygenation of Unactivated sp 3 C- Bonds Pd(Ac) 2 5 mol% PhI(Ac) 2 1.1 eq. Pd 2 Ac Desai, L. P.; ull, K. L.; Sanford *, M. S. University of Michigan J. Am. Chem. Soc. 2004, 126, ASAP
Nine-Step Enantioselective Total Synthesis of (+)-Minfiensine
ine-step nantioselective Total Synthesis of (+)-Minfiensine Jones, S. B.; Simmons, B.; MacMillan, D. W. C.* J. Am. Chem. Soc. 2009, ASAP. DI: 10.1021/ja906472m Kara George Wipf Group - Current Literature
Total Syntheses of Nominine
Total Syntheses of ominine i Literature t Group eting Lizzie Bryan ctober 17, 2007 Aconite Alkaloids Atidane V eatchane Cycloveatchane Aconitane etisan Muratake,. M.; atsume, M.; akai,. Tetrahedron, 2006,
A New Strategy for Efficient Synthesis of Medium and Large Ring Lactones without High Dilution or Slow Addition
A ew Strategy for Efficient Synthesis of Medium and Large ing Lactones without High Dilution or Slow Addition BF 3 Et 2 TIPS 2,4,6-collidine n + n+2 ' ' Zhao, W.; Li, Z; Sun, J. J. Am. Chem. Soc. 2013
Total Synthesis of Trioxacarcin DC-45-A2
Total Synthesis of Trioxacarcin DC-45-A2 icolaou, K. C.; Cai, Q.; Qin, B.; Petersen, M. T.; Mikkelsen,. J. T.; eretsch, P. Angew. Chem. nt. Ed. Engl. 205, 54, 3074 3078. D : 0.002/anie.2040369 Valentin
Suggested solutions for Chapter 40
s for Chapter 40 40 PBLEM 1 Suggest mechanisms for these reactions, explaining the role of palladium in the first step. Ac Et Et BS () 4 2 1. 2. K 2 C 3 evision of enol ethers and bromination, the Wittig
SECTION 12. «POT-POURRI» in Organic Synthesis (2018)
SECTIN 12 «PT-PURRI» in rganic Synthesis (2018) 1 Total Synthesis of Erythromycin A via a Spiroketal ERYTRMYCIN A DESLNGCAMPS et al. Can. J. Chem. 1985, 63, 2810-2820. 2 Tetrahydropyran Derivative as Starting
A Modular Approach to Polyketide Building Blocks: Cycloadditions of Nitrile Oxides and Homoallylic Alcohols
A Modular Approach to Polyketide Building Blocks: Cycloadditions of itrile xides and Homoallylic Alcohols rganic Letters, 2005, ASAP ina Lohse-Fraefel and Erick M. Carreira * H H H + ' 1. t-bucl, -78 C
Total Synthesis of (+)-Sieboldine A J. Am. Chem. Soc. 2010, 132,
Total Synthesis of (+)-Sieboldine A J. Am. Chem. Soc. 2010, 132, 7876 7877. Current Literature Presentation 10JUL2010 Michael Yang Mike Yang @ Wipf Group Page 1 of 15 7/10/2010 Sieboldine A Background
Asymmetric Radical Reactions. Zhen Liu 08/30/2018
Asymmetric adical eactions Zhen Liu 08/30/2018 Contents Introduction eactions Using Chiral Auxiliary Chiral Lewis Acid-diated eactions Transition tal-catalyzed eactions eactions Using Chiral rganocatalysts
Final Exam /340 ( CHEM 6352 Fall %) Name
Final Exam /340 ( CEM 6352 Fall 2012 %) Name Dec. 15 th, 2012 9:30-13:45 You may NT use any references or aids to complete the following with the exception of a chemical model set and the scrap paper that
CEM 852 Final Exam. May 6, 2010
CEM 852 Final Exam May 6, 2010 This exam consists of 7 pages. Please make certain that your exam has all of the necessary pages. Total points possible for this exam are 150. n answering your questions,
Construction of Chiral Tetrahydro-β-Carbolines: Asymmetric Pictet Spengler Reaction of Indolyl Dihydropyridines
Literature Report V Construction of Chiral Tetrahydro-β-Carbolines: Asymmetric Pictet Spengler Reaction of Indolyl Dihydropyridines Reporter Checker Date : Xiao-Yong Zhai : Xin-Wei Wang : 2018-04-02 You,
Total Synthesis of Cyclosporine: Access to N-Methylated Peptides via Isonitrile Coupling Reactions
Total Synthesis of Cyclosporine: Access to -thylated Peptides via Isonitrile Coupling Reactions Xiangyang Wu, Jennifer L. Stockdill, Ping Wang, Samuel J. Danishefsky* J. Am. Chem. Soc. 2010,132, 4098-4100
Total Synthesis of the Chartellines
Total Synthesis of the Chartellines X Y chartelline A, X = Y = chartelline B, X =, Y = chartelline C, X = Y = Mariam Shamszad ovember 1, 2006 Background Chartellines A, B, and C were isolated in the 1980s
Literature Report. A 11-Steps Total Synthesis of Magellanine through a Gold(І)-Catalyzed Dehydro Diels-Alder Reaction
Literature Report 11-Steps Total Synthesis of Magellanine through a Gold(І)-Catalyzed ehydro iels-lder Reaction Reporter: ong-qiang Shen Checker: Cong Liu ate: 2017/06/19 McGee, P.; Bétournay, G.; Barabé,
Literature Report IX. Cho, S. H. et al. Org. Lett. 2016, 18, Cho, S. H. et al. Angew. Chem. Int. Ed. 2017, 56,
Literature Report IX ynthesis of β-aminoboronates by Copper(I)- Catalyzed Addition of Diborylalkanes to Imines Reporter Checker Date : hubo Hu : Xiaoyong Zhai : 2017-9-1818 Cho,. H. et al. rg. Lett. 2016,
Lecture 6: Transition-Metal Catalysed C-C Bond Formation
Lecture 6: Transition-Metal Catalysed C-C Bond Formation (a) Asymmetric allylic substitution 1 u - d u (b) Asymmetric eck reaction 2 3 Ar- d (0) Ar 2 3 (c) Asymmetric olefin metathesis alladium π-allyl
Mesoporous Organosilicas with Acidic Frameworks and Basic Sites in the Pores: An Approach to Cooperative Catalytic Reactions
Literature Report 2009-12-08 Mesoporous rganosilicas with Acidic Frameworks and Basic Sites in the Pores: An Approach to Cooperative Catalytic Reactions Yan Yang Shylesh, S.;* Thiel, W. R.* et al. Angew.
Studies Toward the Total Synthesis of (±)-Noelaquinone
Research Topic Seminar 18 June 2005 Studies Toward the Total Synthesis of (±)-Noelaquinone David Amantini WIPF GRUP The Role of Natural Products in Drug Discovery For thousands of years medicine and natural
Asymmetric Catalysis by Lewis Acids and Amines
Asymmetric Catalysis by Lewis Acids and Amines Asymmetric Lewis acid catalysis - Chiral (bisooxazoline) copper (II) complexes - Monodentate Lewis acids: the formyl -bond Amine catalysed reactions Asymmetric
Synthesis of the Stenine Ring System from Pyrrole
Current Literature Presentation gor psenica 06/18/2011 Synthesis of the Stenine Ring System from Pyrrole Bates, R. W.; Sridhar, S. J. rg. Chem., 2011, 76, 5026 5035 gor psenica @ Wipf Group Page 1 of 16
Zr-Catalyzed Carbometallation
-Catalyzed Carbometallation C C C C ML n C C ML n ML n C C C C ML n ML n C C ML n Wipf Group esearch Topic Seminar Juan Arredondo November 13, 2004 Juan Arredondo @ Wipf Group 1 11/14/2004 Carbometallation
A Simple Introduction of the Mizoroki-Heck Reaction
A Simple Introduction of the Mizoroki-Heck Reaction Reporter: Supervisor: Zhe Niu Prof. Yang Prof. Chen Prof. Tang 2016/2/3 Content Introduction Intermolecular Mizoroki-Heck Reaction Intramolecular Mizoroki-Heck
Total Synthesis of (+/-)-Goniomitine via a Formal Nitrile/Donor-Acceptor Cyclopropane [3 + 2] Cyclization
![Total Synthesis of (+/-)-Goniomitine via a Formal Nitrile/Donor-Acceptor Cyclopropane [3 + 2] Cyclization](/thumbs/82/85235286.jpg "Total Synthesis of (+/-)-Goniomitine via a Formal Nitrile/Donor-Acceptor Cyclopropane [3 + 2] Cyclization")
Total Synthesis of (+/-)-Goniomitine via a Formal itrile/donor-acceptor Cyclopropane [3 + 2] Cyclization (-)-Goniomitine Christian L. Morales and Brian Pagenkopf* rganic Letters, ASAP Current Literature
Total Synthesis of ( )-Virginiamycin M2
Total Synthesis of ( )-Virginiamycin M2 Jie Wu and James S. Panek, Angewandte Chemie International Edition, 2010, 49, 6165-6168 btained from the CDC Public ealth Image Library. Image credit: CDC/Dr. David
JACS ASAP Article: Published 3/12/08. Lei Jiao, Changxia Yuan and Zhi-Xiang Yu. Current Literature: 3/29/08. David Arnold
Tandem h(i)-catalyzed [(5+2)+1] Cycloaddition/Aldol eaction for the Construction of Linear Triquinane Skeleton: Total Syntheses of (+)-irsutene and (+)-1- Desoxyhypnophilin JACS ASAP Article: Published
Short Lit
Short Lit. - 7-12-2010 Jonathan A. Brekan a Department of Chemistry, orthwestern University, 2145 Sheridan Road, 60208, Evanston, Illinois, United States of America Citronellal Monoterpenoid distillate
Total Synthesis of Maoecrystal V: Early-Stage of C-H Functionalization and Lactone
Literature Report Total Synthesis of Maoecrystal V: arly-stage of C- Functionalization and Lactone Assembly by Radical Cyclization Reporter: Ji Yue Checker: Chen Muwang Date: 2013/12/02 Zakarian, A. et
Approaches to the Synthesis. of Tetrahydropyrans. (and closely related heterocycles)
Approaches to the Synthesis of Tetrahydropyrans (and closely related heterocycles) William Morris Literature Presentation July 6, 2004 I. Intro A Nomenclature B Prevalence in Nature C Biosynthetic Considerations
Department of Chemistry, Colorado State University, Fort Collins, Colorado University of Colorado Cancer Center, Aurora, Colorado 80045
Improved Biomimetic Total Synthesis of d,l-stephacidin A Thomas J. Greshock 1 and Robert M. Williams 1,2 * 1 Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523 2 University
A synthesis of strychnine. by a longest linear sequence of six steps. Chem. Sci. 2011, 2, David B. C. Martin and Christopher D.
A synthesis of strychnine by a longest linear sequence of six steps David B. C. Martin and Christopher D. Vanderwal Chem. Sci. 2011, 2, 649-651 ABUT STRYCIE Member of the Strychnos alkaloids isolated in
Lewis Base Activation of Lewis Acids: Development of a Lewis Base Catalyzed Selenolactonization
Lewis Base Activation of Lewis Acids: Development of a Lewis Base Catalyzed Selenolactonization Denmark, S.E. and Collins, W.R. rg. Lett. 2007, 9, 3801-3804. C 2 H + Se Lewis Base CH 2 Cl 2 Se Presented
Catalytic synthesis of amines and amides
Catalytic synthesis of amines and amides Jonathan Williams University of Bath Catalytic approaches to amine synthesis Br Pd or Cu cat 2 Chem. Sci., 2011,27 ' TM or Ln cat 2 ' 2 and/or 2 ' rg. Biol. Chem.,
Syntheses of Leucascandrolide A. Supergroup Meeting August 4 th, 2004 Yu Yuan
Syntheses of Leucascandrolide A Supergroup Meeting August 4 th, 2004 Yu Yuan Leucascandrolide A Me Me Me Dambrosio, M.; Guerriero, A.; Debitus, C.; Pietra, F. elvetica Chimica Acta 1996, 79, 51-60 Me 1
Chiral Brønsted Acid Catalysis
Chiral Brønsted Acid Catalysis Aryl Aryl Aryl Aryl S CF 3 2 P Fe CF 3 CF 3 2 Jack Liu ov. 16, 2004 CF 3 Introduction Chiral Brønsted acid catalysis in nature: enzymes and peptides Chiral Brønsted acid
Prof. Ang Li. Literature Seminar Kosuke Minagawa (D2)
Prof. Ang Li Literature Seminar 2017. 10. 28 Kosuke Minagawa (D2) 1 2 3 aspidodasycarpine 1) 2 C sespenine 3) atural Products Synthesized by Ang Li group clostrubin 6) drimentine A 7) i-bu rubriflordilactone
Organocopper Chemistry
rganocopper Chemistry ave a great historical importance, but still remain highly useful reactions. If not the first organometallic reactions developed they are among the first. Most often used in conjugate
Spiro Monophosphite and Monophosphoramidite Ligand Kit
Spiro Monophosphite and Monophosphoramidite Ligand Kit metals inorganics organometallics catalysts ligands custom synthesis cgm facilities nanomaterials 15-5162 15-5150 15-5156 15-5163 15-5151 15-5157
eatles Oasis - 199
eatles - 1964 asis - 199 Biography 2001-present: University of 1997-2000: Professor, Shef 1988-1997: Various Reader 1986-1988: Post-doc with G 1983-1986: D at Universi 1983: Undergrad at Cambrid Enantioselective
Copper-Catalyzed Synthesis of Esters from Ketones. Alkyl Group as a Leaving Group.
Copper-Catalyzed Synthesis of Esters from Ketones. Alkyl Group as a Leaving Group. akatani, Y.; Koizumi, Y.; Yamasaki, R.; Saito, S. rg. Lett. 2008, 10, 2067-2070. An Annulation Reaction for the Synthesis
Total Synthesis of ( )-Himandrine
Total Synthesis of ( )-imandrine M. Movassaghi,* M. Tjandra and J. Qi J. Am. hem. Soc. 2009, 131, 9648-9650 Bz Adam T. oye urrent Literature ctober 3, 2009 Adam oye @ Wipf Group Page 1 of 22 10/3/2009
Comparative Synthesis of Ingenol. Tyler W. Wilson SED Group Meeting
Comparative Synthesis of Ingenol Tyler W. Wilson SED Group eting 2.27.07 Ingenol: Biology, Isolation, and istory During WWII a latex was manufactured by precipitating the milky juice of the Euphorbia Ingen
Metal Catalyzed Outer Sphere Alkylations of Unactivated Olefins and Alkynes
Metal Catalyzed uter Sphere Alkylations of Unactivated lefins and Alkynes Stephen Goble rganic Super-Group Meeting Literature Presentation ctober 6, 2004 1 utline I. Background Introduction to Carbometallation
Concise, Asymmetric, Stereocontrolled Total Synthesis of Stephacidins A, B and Notoamide B
Concise, Asymmetric, Stereocontrolled Total Synthesis of Stephacidins A, B and otoamide B (+)-avrainvillamine (+)-notoamide B 20 51 21 55 (-)-stephacidin B In 2002, Bristol-Myers Squibb reported the biologically
Synthesis of Azadirachtin: A Long but Successful Journey
ynthesis of Azadirachtin: A Long but uccessful Journey Gemma E. Veitch, Edith Beckmann, Brenda J. Burke, Alistair Boyer, arah L. Maslen, and teven V. Ley Angew. Chem. Int. Ed. 2007, Early View And Gemma
Development of Chiral Phosphine Olefin Ligands and Their Use in Asymmetric Catalysis
Development of Chiral osphine lefin Ligands and Their Use in Asymmetric Catalysis 2 Wei-Liang Duan July 31, 2007 Research Works in Hayashi Group, Kyoto University (ct, 2003 Mar, 2007) Conventional Chiral
Stereocontrolled organocatalytic synthesis of prostaglandin PGF 2 in seven steps
Stereocontrolled organocatalytic synthesis of prostaglandin PGF 2 in seven steps Graeme Coulthard, William Erb, Varinder K. Aggarwal Nature. August 15, 2012. DI: 10.1038/nature11411 N C 2 then [Bn 2 N
Heterocyclic Chemistry
Dr. P. Wipf Page 1 of 8 10/24/2009 eterocyclic Chemistry Most Common Aromatic Scaffolds Present in Bioactive Molecules S S S S rtl, P.; Jelfs, S.; Muehlbacher, J.; Schuffenhauer, A.; Selzer, P., "Quest
Synthesis of Abyssomicin C. Marie-Caroline Cordonnier Litterature Review 23/01/2009
Synthesis of Abyssomicin C Marie-Caroline Cordonnier Litterature Review 23/01/2009 Isolation Isolated in 2004 from the actinomycete Verrucosispora strain collected from a sediment at a depth of 289m in
Studies on Heck and Suzuki Reactions Catalyzed by Palladium(0) and Wacker- Type Oxidative Cyclization Catalyzed by Palladium(II)
Studies on eck and Suzuki Reactions Catalyzed by Palladium(0) and Wacker- Type xidative Cyclization Catalyzed by Palladium() Zuhui Zhang enmark Group Meeting 10/21/2008 1 Part ne: Palladium(0)-Catalyzed
Ladderanes: Uses and Synthesis. Nicholas Anderson Denmark Group Meeting October 28, 2008
Ladderanes: Uses and Synthesis icholas Anderson Denmark Group Meeting ctober 28, 2008 utline Ladderane types and classifications Potential applications of ladderanes Synthesis of ladderanes Ladderane natural
Intramolecular Huisgen-Type Cyclization of Platinum-Bound Pyrylium Ions with Alkenes and Subsequent Insertion into a Benzylic C-H Bond
Intramolecular uisgen-type Cyclization of Platinum-Bound Pyrylium Ions with Alkenes and Subsequent Insertion into a Benzylic C- Bond Chang o h,* Ji o Lee, Su Jin Lee, Jae Il Kim, and Chang Seop ong Department
Some questions and answers that we will get out of this example synthesis:
UTLINE 535 LECTURE 3 (2004) Page 22 The Synthesis of Cubane I am showing you this synthesis because it is elegant and exemplifies many different concepts. We can use it to talk in context about the philosophical
Asymmetric Nucleophilic Catalysis
Asymmetric ucleophilic Catalysis Chiral catalyst X 2 Chiral catalyst X = alkyl, X 1 2 1 Vedejs, E.; Daugulis,. J. Am. Chem. Soc. 2003, 125, 4166-4173 Shaw, S. A.; Aleman,.; Vedejs, E. J. Am. Chem. Soc.
A 1,3 Strain and the Anomeric Effect. Michael Shaghafi Chem. Topics Feb. 6, 2012
A 1,3 Strain and the Anomeric Effect Michael Shaghafi Chem. Topics Feb. 6, 2012 Introduction: Definition of A 1,3 Strain m L L m m 3 L 3 1 1 otation about σ-bond between α-stereocenter and olefin is associated
Organo-transition Metal Chemistry
Prof. Dr. Burkhard König, nstitut für rganische Chemie, Universität egensburg 1 rgano-transition tal Chemistry 1. Some Basics Chemistry involves intermediates containing transition-metal carbon bonds tal-carbon
Epoxidation with Peroxy Acids
Epoxidation with Peroxy Acids RC 3 R C more reactive more likely Freccero, M.; Gandolfi, R.; Sarzi-Amadè, M.; Rastelli, A. J. rg. Chem. 2000, 65, 2030. Singleton, D. A.; Merrigan, S. R.; Liu, J.; ouk,
Chiral Bronsted Acids as Catalysts
Chiral Bronsted Acids as Catalysts Short Literature Seminar 6/3/08 Dustin aup BIL Derived osphoric Acids - First reported in 1992 as a ligand by irrung and coworkers. 4 h 2 irrung Tet. Lett. 1992, 33,
Enan$oselec$ve Total Synthesis of Amphidinolide F
Enan$oselec$ve Total Synthesis of Amphidinolide F Subham Mahapatra and ich G. Carter regon State University Angew. Chem. nt. Ed., 2012, 51, 7948 Nicolas Millius Bern, 07.02.2013 ntroduc$on isolated from
Convergent Route to ent-kaurane Diterpenoids: Total Synthesis of Lungshengenin D and 1α6α- Diacetoxy-ent-kaura-9(11),16-dien- 12,15-dione
Convergent Route to ent-kaurane Diterpenoids: Total Synthesis of Lungshengenin D and 1α6α- Diacetoxy-ent-kaura-9(11),16-dien- 12,15-dione Xiangbo Zhao, Wu Li, Junjie Wang, and Dawei Ma* Shanghai Institute
Radical Reactions. Radical Stability!!! bond dissociation energies X Y X + Y. bond BDE (kcal/mol) bond BDE (kcal/mol) CH 3 CH 3 CH 2 95 O H R 2 C H
adical eactions adical Stability!!! bond dissociation energies X Y X Y bond BDE (kcal/mol) bond BDE (kcal/mol) C 3 104 108 C 3 C 2 98 110 95 2 C 102 (-) 93 (C-) 92 C 3 C 3 36 89 85 C 3 C 3 80 adical eactions
Use of Cp 2 TiCl in Synthesis
Use of 2 TiCl in Synthesis eagent Control of adical eactions Jeff Kallemeyn May 21, 2002 eactions of 2 TiCl 1. Pinacol Coupling H H H 2. Epoxide pening H H E H Chemoselectivity Activated aldehydes (aromatic,
Ynolate Chemistry. Jeff Kallemeyn October 22, 2002
Ynolate Chemistry While enolates have numbered among the most important reagents of organic chemistry for more than a century, ynolates have hitherto remained unknown although their chemistry should be
Organic Tutorials 3 rd Year Michaelmas Transition Metals in Organic Synthesis: (General paper level) ! 1! Reading
rganic Tutorials 3 rd Year Michaelmas 2010 Transition Metals in rganic Synthesis: (General paper level) Reading 1. Lecture Course, and suggested references from this. 2. Clayden, Greaves, Warren and Wothers.
Massachusetts Institute of Technology Organic Chemistry 5.512
Massachusetts Institute of Technology rganic Chemistry 5.512 Problem Set 6 Solutions Stereocontrolled Carbonyl Reduction and Aldol Reactions May 5, 2006 Lucy Kohnen ( The target compound was used as an
A Concise Synthesis of ( )- Aplyviolene Facilitated by a Stragetegic Ter<ary Radical Conjugate Addi<on
A Concise Synthesis of ( )- Aplyviolene Facilitated by a Stragetegic Ter
Chem 253 Problem Set 7 Due: Friday, December 3, 2004
Chem 253 roblem Set 7 ue: Friday, ecember 3, 2004 Name TF. Starting with the provided starting material, provide a concise synthesis of. You may use any other reagents for your synthesis. It can be assumed
Organocatalytic Umpolung via N- Heterocyclic Carbenes. Qinghe Liu Hu Group Meeting August 20 th 2015
rganocatalytic Umpolung via N- Heterocyclic Carbenes Qinghe Liu Hu Group Meeting August 20 th 2015 Contents Part 1: Introduction Part 2: N-Heterocyclic carbene-catalyzed umpolung: classical umpolung, conjugated
STRATEGIES IN SYNTHESIS
STRATEGIES I SYTESIS Professor T. J. Donohoe MT 2006 6 Lectures: Tuesday at 10 am; Thursday at 9 am (weeks 6-8) DP: Lecture Theatre Monensin Me 7 Et Me Me Me Me Me Me C 2 1 Me Kishi J. Am. Chem. Soc, 1979,
!"#$%&&'!&(!)*+,-./!01"2.3$*4!"!#$!%$!%&'(') *+,!-$!%&'(').!'/ *&%&*,$.&-!"!3$!4$!5)01+!.*!06'2
!"#$%&&'!&(!)*+,-./!01"2.3$*4!"!#$!%$!%&'(') *+,!-$!%&'(').!'/012 546*&%&*,$.&-!"!3$!4$!5)01+!.*!06'2 C-C Bond Formation: Cross-coupling Reaction of rganometal Compounds with rganic alids M C-m + X-C C-C
Stable gold(iii) catalysts by oxidative addition of a carboncarbon
Stable gold(iii) catalysts by oxidative addition of a carboncarbon bond Chung-Yeh Wu, Takahiro oribe, Christian Borch Jacobsen & F. Dean Toste ature, 517, 449-454 (2015) presented by Ian Crouch Literature
A Review of Total Synthesis of Spirotryprostatin A and B. Jinglong Chen Supergroup meeting Princeton University June
A Review of Total Synthesis of Spirotryprostatin A and B Jinglong Chen Supergroup meeting Princeton University June 28 2006 ovel Mammalian Cell Cycle Inhibitors, Spirotryprostatins A and B Me Spirotryprostatin
Total Synthesis of the Sesquiterpenoid Periconianone A Based on a Postulated Biogenesis
Total Synthesis of the Sesquiterpenoid Periconianone A Based on a Postulated Biogenesis C 3 C3 Liffert, R., Linden, A., Gademann, K. J. Am. Chem. Soc. 2017, 139, 16096 Presented by: Brendyn Smith CEM 852
i-pr 2 Zn CHO N Sato, I.; Sugie, R.; Matsueda, Y.; Furumura, Y.; Soai, K. Angew. Chem., Int. Ed. Engl. 2004, 43, 4490
Asymmetric Synthesis Utilizing Circularly Polarized Light Mediated by the otoequilibration of Chiral lefins in Conjuction with Asymmetric Autocatalysis l-cpl r-cpl (S) () Sato, I.; Sugie,.; Matsueda, Y.;