Highly Cytotoxic, Structure Similar Polyke>des CO 2 H
|
|
|
- Lynn Daniels
- 5 years ago
- Views:
Transcription
1 Current Literature Anguinomycins and Deriva2ves: Total Syntheses, Modeling, and Biological Evalua2on of the Inhibi2on of Nucleocytoplasmic Transport liv Eidam, Ulrike Kutay, Karl Gadermann, et al, JACS, ASAP, 2010 Junyan an Dr. Wipf Group Jan. 23, Junyan Wipf Group Page 1 of 14 1/27/2010
2 ' Anguinomycin A: = C 3, ' = C 2 Anguinomycin B: = C 2 5, ' = C 2 Anguinomycin C: = C 3, ' = C 3 Anguinomycin D: = C 2 5, ' = C 3 Isolated from Streptomyces strains IC nm against normal and transformed rat cells Selec>ve induce apoptosis of p B inac>vated tumor cells, while inducing growth arrest in normal cells Inhibits nucleocytoplasmic transport ayakawa, Y, et al, J. An>biot. 1987, 40, 1349; ayakawa, Y, et al, J. An>biot. 1995, 48, Junyan Wipf Group Page 2 of 14 1/27/2010
3 ' C 2 Anguinomycin A: = C 3, ' = C 2 Anguinomycin B: = C 2 5, ' = C 2 Anguinomycin C: = C 3, ' = C 3 Anguinomycin D: = C 2 5, ' = C 3 IC 50 = nm Leptomycin B (LMB) over 1000 pubs C 2 (-)-Kazusamycin A (-)-Callystatin A IC 50 = 10PM C ighly Cytotoxic, Leptofuranin D Structure Similar Polyke>des 3 Junyan Wipf Group Page 3 of 14 1/27/2010
4 etro Synthesis Negishi coupling Wittig eaction Evans Syn-aldol Jacobson's Cr(III) etero D-A B-alkyl Suzuki-Miyaura Coupling Me Br PPh Br Et 3 Br TES TIPS A B C D E 4 Junyan Wipf Group Page 4 of 14 1/27/2010
5 Synthesis of C1 C11 Fragment Me Cp 2 ZrCl; ZnCl 2 ; Pd(PPh 3 ) 4, DIBA then b 81 % Me 2.3 mol% a + 4 A MS, r.t. TES 86 % i Pr Br TIPS 96 % ee TES Pd(PPh 3 ) 4, Me 2 Zn or PdCl 2 (dpeps) Et 2 Zn, TF 1. PTSA, i Pr 2. TBAF, TF 84 % i Pr i Pr = Me, 68 % = Et, 84 % TIPS TBAF; PPh 3, imidazole I 2, toluene, ether i Pr = Me, 75 % = Et, 88 % I N Cr Cl a Br Br b TIPS 5 Junyan Wipf Group Page 5 of 14 1/27/2010
6 Me ighly Enan>o and egioselec>ve Quinone Diels Alder eac>ons Catalyzed by a Tridentate Schiif Base CrIII Complex + Me TES Me 5 mol% a toluene, 0 ºC Me TES DBU, air Me TES Me Me Me Me TES TES TES 96 % ee 12:1 93 % ee > 30:1 97 %ee 25:1 90 % ee 9:1 E. Jacobson, et al, ACIE, 2005, 6043 E. Jacobson, et al, ACIE, 2005, 6047 Me Me Me Me Colombiasin A N Cr Cl a 6 Junyan Wipf Group Page 6 of 14 1/27/2010
7 i Pr Negishi Coupling with Selec>ve Inversion and eten>on of the Configura>on Br TIPS 5-10 mol% catalyst Et 2 Zn, M i Pr TIPS + i Pr TIPS 7 Junyan Wipf Group Page 7 of 14 1/27/2010
8 Synthesis of C12 C24 Fragment N Br N 1. LA, Et 2, 0 ºC Ph Ph c LDA, -78 ºC Ph Ph 92 % dr > 97:3 2. xalyl chloride, DMS C 2 Cl 2, then Et 3 N 99 % ent-c, Bu 2 BTf, Et 3 N 77 % Ph Ph N dr > 87:13 1. MeNMe Cl, AlMe3 2. TBSTf, 2,6-lutidine 3. DIBA 86 % TBS PPh 1. ent-c, Bu TBS Et 3 2 BTf,Et 3 N 2. LA, toluene, -17 ºC toluene, ºC 99 % 99 % Et dr > 97:3 TBS 1. DIBA, TF, -78 to -10 ºC I TBS 2. Mn 2, C 2 Cl 2 3. CrCl 2, CI 3, TF, 0 ºC 75 % dr > 97:3 8 Junyan Wipf Group Page 8 of 14 1/27/2010
9 Comple>on of the Synthesis i Pr I 9-Me-9-BBN, tbuli ether, -78 ºC to r.t. i Pr B + I TBS Me = C 3 or C mol% Pd(dppf)Cl 2 C 2 Cl 2 i Pr 1. PPTS, water, acetone 15 mol% AsPh 3, Cs 2 C 3 2, DMF = C 3, 80% = C 2 5, 48 % TBS 2. = C 3, DMP, then Mn 2 or = C 2 5, PCC 3. F pyridine, pyridine 4.5 d Anguinomycin C 30 % Anguinomycin D 57 % 9 Junyan Wipf Group Page 9 of 14 1/27/2010
10 i Pr mixture fraction 17 TBS Compounds Generated Using a Mixture of Diastereoisomers at C17 Anguinomycin D (2) Junyan Wipf Group Page 10 of 14 1/27/2010
11 Biological Evalua>on as Inhibitor of Nucleocytoplasmic Transport = C3, 1 = C25, 2 44 C2 LMB ela cell and io2 protein Junyan Wipf Group Page 11 of 14 1/27/2010
12 Chromosome maintenance region 1 (CM1) and SNUPN Complex A. X-ay structure of the CM1-SNUPN complex B. Close-up view on the N-terminal nuclear export signal (NES) of SNUPN C. ydrophobic residues of SNUPN NES define five pockets in the CM1 groove 12 Junyan Wipf Group Page 12 of 14 1/27/2010
13 Models of CM1 Inhibitor Complex Sphere models of Leptomycin B adduct (A) and compound 4 adduct (B). C. Superposition of LMB adduct with NES residues of SNUPN. LMB depicted in yellow with hydrogen white. D. Atom numbering of LMB adduct. 13 Junyan Wipf Group Page 13 of 14 1/27/2010
14 Conclusion Total synthesis of Anguinomycin C (6.7%) and D (6%)were obtained in 18 steps (longest linear sequence). Inhibitors of CM1, shut down protein export at > 10 nm Structure basis for this inhibi>on. Lactone ring and side chain effects. 14 Junyan Wipf Group Page 14 of 14 1/27/2010
I. Liu Lab. Ka<e Boknevitz 1
A ighly Convergent Total Synthesis of Leustroducsin B Barry M. Trost,* Berenger Biannic, Cheyenne S. Brindle, B. Michael Keefe, Thomas J. unger, and Ming-Yu gai Department of Chemistry, Stanford University,
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
Large-Scale Synthesis of the Anti-Cancer Marine Natural Product (+)-Discodermolide
61.7 g prepared in 39 steps 43 chemists worked on the project which lasted 20 months Chris Kendall @ Wipf Group 1 3/27/04 8 22 1 5 24 carbon linear polypropionate chain containing stereocenters (6 hydroxyl
Hennoxazole A. Philip Williams Group Meeting December 12, OMe. OMe 1 6 O H
ennoxazole A 1 6 11 17 24 Philip Williams Group eting December 12, 2007 Discovered Discovered by Paul cheuer at the University of awaii in 1991. Isolated 480mg ennoxazole A from 4.5kg from the sponge Polyfibrospongia
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.
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
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
Total Synthesis of Rapamycin
. sman, CEM 20 //2007 Total ynthesis of Rapamycin Matthew L. Maddess, Miles. Tackett, idenori Watanabe, Paul E. ennan, Christopher D. pilling, James. cott, David P. sborn, and teven V. Ley* Angew. Chem.
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
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
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
Negishi Coupling of Secondary Alkylzinc Halides with Aryl Bromides and Chlorides
Negishi Coupling of Secondary Alkylzinc alides with Aryl Bromides and Chlorides X X = Br, Cl 2 1 ZnBr 1, 2 = Alkyl Cat. Pd(OAc) 2 Ligand TF/Toluene rt or 60 o C 1 2 J. Am. Chem. Soc. 2009, ASAP Article
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
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
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
Synthesis of Amphidinolide X and an Exploration of Key Reactions
PJM 1/12/05 Synthesis of Amphidinolide X and an Exploration of Key eactions Lepage,.; Kattnig, E.; Furstner, A. JACS, 2004, 126, 15970-15971. 7 13 1 6 19 - Produced by marine dinoflagellates, Amphidinium
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.
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
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,
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
Total Synthesis of (-)-Mersicarpine
Total Synthesis of (-)-Mersicarpine Rie akajima, Tsuyoshi gino, Satoshi Yokoshima, and Tohru Fukuyama. J. Am. Chem. Soc. ASAP Published online 1-7-2010 Eric E. Buck Current Literature January 23, 2010
TMSCl imidazole DMF. Ph Ph OTMS. Michael reaction. Michael reaction Ph R 3. epoxidation O R
eaction using diarylprolinol silyl ether derivatives as catalyst 1) C Et K C 3, ) MgBr, TF TMS hexane, 0 o C TBS p- C 6 4, T C Et 85%, 99% ee Angew. Chem., nt. Ed., 44, 41 (005). rg. Synth., 017, 94, 5.
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
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
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.
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
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.
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
An Analysis of the Total Syntheses of Aphidicolin
An Analysis of the Total Syntheses of Aphidicolin An Evans Group Afternoon Seminar Krista Beaver March 20, 1998 A B D C Aphidicolin Isolated from the fungus Cephalosporium aphidicola (esp, Chem. Comm.1972,
Stereocontrolled Synthesis of Kalihinol C Christopher A. Reiher and Ryan A. Shenvi
Stereocontrolled Synthesis of Kalihinol hristopher A. eiher and yan A. Shenvi Department of hemistry, The Scripps esearch Institute, La Jolla, alifornia 9703, USA ameron Mconnell Professor S.-Y. Liu 05/03/017
CuI CuI eage lic R tal ome rgan gbr ommon
Common rganometallic eagents Li Et 2 Li Mg Et 2 Li alkyllithium rignard Mg Mg Li Zn TF ZnCl 2 TF dialkylzinc Zn 2 2 Zn Li CuI TF ganocuprate CuI 2 2 CuI common electrophile pairings ' Cl ' '' ' ' ' ' '
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,
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
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
Total Synthesis of Peloruside A Through Kinetic Lactonization and Relay Ring-Closing Metathesis Cyclization Reactions
Total Synthesis of Peloruside A Through Kinetic Lactonization and Relay Ring-Closing Metathesis Cyclization Reactions Thomas R. oye, Junha Jeon, Lucas C. Kopel, Troy D. Ryba, Manomi A. Tennakoon, and Yini
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
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
CEM 852 Final Exam. May 5, 2011
CEM 852 Final Exam May 5, 2011 This exam consists of 8 pages. Please make certain that your exam has all of the necessary pages. Total points possible for this exam are 150. In answering your questions,
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
Approaches to the Synthesis of Macquarimicins and Cochleamycins
Ac Macquarimicin A Cochleamycin A Approaches to the Synthesis of Macquarimicins and Cochleamycins Drew Adams Friday Seminar March 18, 2005 Isolation and Activity Ac Isolated in 1995 from Micromonospora
James D. White. A very productive professor 64 students graduated from his lab 94 postdocs have worked in his lab. Education Experience
A very productive professor 64 students graduated from his lab 94 postdocs have worked in his lab Education Experience Fraser Fleming University of Drexel Pavel agory University of Michigan Cambridge University,
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
Total synthesis of Spongistatin
Literature Semminar 1. Introduction: Total synthesis of Spongistatin Chen Zhihua (M2) Isolation: Pettit et al. J. rg. Chem. 1993, 58, 1302. Kitagawa et al. Tetrahedron Lett. 1993, 34, 1993. Fusetani et
Progress toward the Total Synthesis of Pleurotin
Progress toward the Total Synthesis of Pleurotin SINYA IIMURA Wipf Research Group Meeting July 9th, 2005 Shinya Iimura @ Wipf Group 1 7/10/2005 Presentation utline! Isolation and Structure! Biological
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
Tips for taking exams in 852
Comprehensive Tactical Methods in rganic Synthesis W. D. Wulff 1) Know the relative reactivity of carbonyl compounds Tips for taking exams in 852 Cl > > ' > > ' N2 eg: 'Mg Et ' 1equiv. 1equiv. ' ' Et 50%
The Amphidinolide T-Series
How a Total ynthesis Evolves ver Time The Amphidinolide T-eries H Jason M. tevens 12/06/2006 Amphidinolide Natural Products Isolated in 2000 from marine dinoflagellates of the genus Amphidinium living
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
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
Total Synthesis of Callipeltoside A. Denmark Group Meeting Aaron Bailey September 23, 2008
Total Synthesis of Callipeltoside A Denmark Group eting Aaron Bailey September 23, 2008 Callipeltoside A First isolated from Lithistid sponge in 1996 Exhibits moderate cytotoxicity against human bronchopulmonary
Organic Cumulative Exam October 13, 2016
rganic Cumulative Exam ctober 3, 206 Answer only three of the five questions. o more than three question answers will be graded and any work not to be considered must be clearly marked as such. Clearly
CHEM 330. Final Exam December 11, This a closed-notes, closed-book exam. The use of molecular models is allowed. This exam contains 12 pages
CEM 330 Final Exam December 11, 2007 Your name: This a closed-notes, closed-book exam The use of molecular models is allowed This exam contains 12 pages Time: 2h 30 min 1. / 20 2. / 20 3. / 30 4. / 40
Synthesis of Polyfluorinated and Polychlorinated Hydrocarbons
Synthesis of Polyfluorinated and Polychlorinated Hydrocarbons Yong Guan Feb. 13, 2009 Nicoletti, M.; O Hagan, D.; Slawin, A.M.Z. J. Am. Chem. Soc. 2005, 127, 482. Hunter, L.; O Hagan, D.; Slawin, A.M.Z.
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,
CEM 852 Exam-2 April 11, 2015
CEM 852 Exam-2 April 11, 2015 This exam consists of 6 pages. Please make certain that your exam has all of the necessary pages. Total points possible for this exam are 100. In answering your questions,
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
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
2.222 Practice Problems 2003
2.222 Practice Problems 2003 Set #1 1. Provide the missing starting compound(s), reagent/solvent, or product to correctly complete each of the following. Most people in the class have not done this type
Synthesis of the Phomoidrides (CP 225,917 & CP 263,114) Chem. Rev. 2003, 103, 2691.
ynthesis of the Phomoidrides (P 225,917 & P 263,114) hem. Rev. 2003, 103, 2691. 15 7 26 2 7 16 14 1 2 5 7 2 7 1 2 1 4 2 6 1 5 9 1 7 1 9 2 9 1 5 (+)-P hom oidr ide A ; 7 = (P- 225,917) (+)-P hom oidr ide
Final Exam /415 ( CHEM 6352 Fall %) Name
Final Exam /415 ( CEM 6352 Fall 2011 %) Name Dec. 15 th, 2011 8:00-12:00 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
Synthetic Developments Towards the Preparation of Erythromycin and Erythronolide Derivatives
ynthetic Developments Towards the Preparation of Erythromycin and Erythronolide Derivatives Russell C. mith Denmark Group Meeting 8-9-2005 most extensive project in organic synthesis this phenomenon is
Palladium-Mediated Functionalization of Heteroaromatic Cations: Comparative Study on Quinolizinium Cations
Palladium-Mediated Functionalization of Heteroaromatic Cations: Comparative Study on Quinolizinium Cations Domingo Garcia-Cuadrado, Ana M. Cuadro, Bernado M. Barchin, Ana unez, Tatiana Caneque, Julio Alvarez-
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
Scandium-Catalyzed Asymmetric Reactions
Scandium-Catalyzed Asymmetric eactions Jimmy Wu Evans Group Seminar February 11, 2005 I. Background II. eutral BIL Ligands III. Anionic BIL Ligands IV. Pybox Ligands V. Bip yridine Ligands VI. rganop hosp
Total Synthesis of (-)-Anominine
Total Synthesis of (-)-Anominine Ben Bradshaw, Gorka Etxbarria-Jardí and Josep Bonjoch* Laboratori de Química rgànica, Facultat de Farmàci, Universitat de Barcelona, Barcelona, Spain J. Am. Chem. Soc.
A Highly Convergent and Biomimetic Total Synthesis of Portentol
A ighly Convergent and Biomimetic Total Synthesis of Portentol portentol B. Cheng, D. Trauner, J. Am. Chem. Soc. 2015, 137, 13800 13083 Departement of Chemistry and Center for Integrated Protein Science
Synthesis of Substituted 1,4-Dienes by Direct Alkylation of Allylic Alcohols Kolundzic, F.; Micalizio, G. C. J. Am. Chem. Soc. 2007, 129,
Synthesis of Substituted 1,4-Dienes by Direct Alkylation of Allylic Alcohols Kolundzic, F.; Micalizio, G. C. J. Am. Chem. Soc. 2007, 129, 15112-15113. Total Synthesis and Structure Elucidation of (+)-orbasin
Chapter 13: Alcohols and Phenols
Chapter 13: Alcohols and Phenols [ Chapter 9 Sections: 9.10; Chapter 13 Sections: 13.1-13.3, 13.9-13.10] 1. Nomenclature of Alcohols simple alcohols C3 C3C2 Eddie Sachs 1927-1964 larger alcohols find the
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
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
Copper-Catalyzed Reaction of Alkyl Halides with Cyclopentadienylmagnesium Reagent
Copper-Catalyzed eaction of Alkyl Halides with Cyclopentadienylmagnesium eagent Mg 1) cat. Cu(Tf) 2 i Pr 2, 25 o C, 3 h 2) H 2, Pt 2 Masahiro Sai, Hidenori Someya, Hideki Yorimitsu, and Koichiro shima
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)
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
CHEMISTRY MIDTERM # 2 November 02, The total number of points in this midterm is 100. The total exam time is 120 min (2 h). Good luck!
CEMISTRY 314-01 MIDTERM # 2 November 02, 2009 Name... The total number of points in this midterm is 100. The total exam time is 120 min (2 h). Good luck! 1. (8 pts) Mark as true (T) or false (F) the following
A Unified Strategy to ent-kauranoid Natural Products: Total Syntheses of ( )-Trichorabdal A and ( )-Longikaurin E
A Unified Strategy to ent-kauranoid Natural Products: Total Syntheses of ( )-Trichorabdal A and ( )-Longikaurin E John T. S. Yeoman, Victor W. Mak, and Sarah E. Reisman. J. Am. Chem. Soc. 2013, 135, 11764.
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
QUESTION PAPER CHEMISTRY-CY
Q.1 Q.5 : Carry E mark each. CEMISTRY-CY 1. Jahn-Teller distortion of CuS 4.5 acts to Raise symmetry Remove an electronic degeneracy Cause loss of ligand Promote a d-electron to an antibonding molecular
Reporter: Yue Ji. Date: 2016/12/26
Literature Report (11) Total Synthesis of Rubriflordilactone B Reporter: Yue Ji Checker: Mu-Wang Chen Date: 2016/12/26 Yang, P.; Yao, M.; Li, J.; Li, Y.; Li, A.* Angew. Chem. Int. Ed. 2016, 55, 6964. Laboratory
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
Short Access to (+)-Lupinine and (+)-Epiquinamide via Double Hydroformylation
Short Access to (+)-Lupinine and (+)-Epiquinamide via Double Hydroformylation Kai Gao Checker: Changbin Yu Mann, A.* et al rg. Lett. 2009, ASAP Strategy for the formation of quinolizidine alkaloids R H
VINBLASTINE. H MeO 2 C MeO. OAc. CO 2 Me. Me H
VIBLATIE 2 C 1 C 2 Ac a 3: catharanthine C 2 Ac C 2 2: ( )-vindoline xidation 5' 2 C 3' 16' 20' Ac C 2 1: (+)-vinblastine b 4 C 2 TFAA, -50 C Polonovski fragmentation 6' 5' 16' C 2 5 TFA 4' 3' 15' 16'
ASYMMETRIC PALLADIUM-CATALYZED ALKENE CARBOAMINATION REACTIONS FOR THE SYNTHESIS OF CYCLIC SULFAMIDES
AYMMETIC PALLADIUM-CATALYZED ALKEE CABAMIATI EACTI F TE YTEI F CYCLIC ULFAMIDE Chem. Eur. J. 2016, 22, 5919 5922 Zachary J. Garlets, Kaia. Parenti, and John P. Wolfe James Johnson Wipf Group Current Literature
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
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.
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,
Chapter 12. Alcohols from Carbonyl Compounds Oxidation-Reduction & Organometallic Compounds. Structure
Chapter 12 Alcohols from Carbonyl Compounds xidation-eduction & rganometallic Compounds Created by Professor William Tam & Dr. Phillis Chang Structure ~ 120 o ~ 120 o C ~ 120 o Carbonyl carbon: sp 2 hybridized
Classics in Tetrahedron Letters
Classics in Tetrahedron Letters Jeremy Richter Baran Group Meeting: 9/24/03 The Plan Methodology Protecting Groups atural Products Syntheses Methodology xidation of Vicinal Diols R R' R'' 1. Cl 2, DMS,
Nickel-Catalyzed Three-Component [3+2+2] Cocyclization of Ethyl Cyclopropylideneacetate and Alkynes
![Nickel-Catalyzed Three-Component [3+2+2] Cocyclization of Ethyl Cyclopropylideneacetate and Alkynes](/thumbs/77/74720708.jpg "Nickel-Catalyzed Three-Component [3+2+2] Cocyclization of Ethyl Cyclopropylideneacetate and Alkynes")
Nickel-Catalyzed Three-Component [3+2+2] Cocyclization of Ethyl Cyclopropylideneacetate and Alkynes Selective Synthesis of Multisubstituted Cycloheptadienes 1 2 Cat. Ni 0 1 2 Komagawa, S.; Saito, S. Angew.
Concise Total Synthesis of Variocolortides A and B through an Unusual Hetero-Diels- Alder Reaction!
Concise Total Synthesis of Variocolortides A and B through an Unusual etero-diels- Alder Reaction! Christian A. Kuttruff, endrik Zipse, and Dirk Trauner! ACIE Early View, DI: 10.1002/anie.201006154! Marija
Suggested solutions for Chapter 41
s for Chapter 41 41 PBLEM 1 Explain how this synthesis of amino acids, starting with natural proline, works. Explain the stereoselectivity of each step after the first. C 2 C 2 3 CF 3 C 2 2 Pd 2 C 2 +
ISOCHRYSOHERMIDIN. MeO 2 C. MeO. MeO. MeO 2 C OH. Me 1
ISCRYSERMIDI 2 C 2 C 1 ormal demand Diels-Alder (M diene - LUM dienophile ) eutral Diels-Alder Inverse demand Diels-Alder (LUM diene - M dienophile ) EDG EWG EWG EDG LUM LUM LUM M E 1 E 2 E 3 M M E Scheme
Enantioselective Synthesis of (+)-Cephalostatin 1
1 Cephalostatin 1 Enantioselective Synthesis of (+)-Cephalostatin 1 Tingting Mo Wipf Group Current Lit. Dec. 26 2009 Tingting Mo @ Wipf Group Page 1 of 9 /28/2009 2 Background 1972, marine worm Cephalodiscus
Midterm Exam #1 /280 CHEM 6352 Fall 2011
Midterm Exam #1 /280 CEM 6352 Fall 2011 ( %) Name Sept 30 th, 2011 18:00-21:00 You may NT use any references or aids to complete the following with the exception of a chemical model set and the scrap paper
JOC: 1985 Year in Review
Baran Group eting JC: 1985 Year in eview Syntheses discussed: thodoligies discussed: Quadrone 2 C (+)-irsutic Acid C (±) Coriolin (!)-Longifolene (!)-astanecine Manganese (III)-mediated "-lactone annulation
Strategies for Stereocontrolled Synthesis
Chemistry. Synthetic rganic Chemistry II Lecture 3 March, 2007 Rick L. Danheiser Massachusetts Institute of Technology! Thermodynamic Control Strategies! Kinetic Control Strategies! Strategies for the
Denmark Group Meeting. & Electrophilic rearrangement of amides
Denmark Group Meeting Palladium catalyzed Dearomatizationeaction & Electrophilic rearrangement of amides 11 th Bo Peng th Feb. 2014 1 https://maps.google.com 2 Palladium catalyzed Dearomatization eaction
Asymmetric Copper-Catalyzed Synthesis of α-amino Boronate Esters from N-tert- Butanesulfinyl Aldimines
Asymmetric Copper-Catalyzed Synthesis of α-amino Boronate Esters from -tert- Butanesulfinyl Aldimines R BR 2 J. Am. Chem. Soc. 2008, 130, 6910. Melissa A. Beenen, Chihul An, and Jonathan A. Ellman rrent
Problem session (3) Daiki Kuwana. Please fill in the blank and explain reaction mechanisms and stereoselectivities.
Problem session (3) Daiki Kuwana Please fill in the blank and explain reaction mechanisms and stereoselectivities. 1. 1-1 1. (Ac) 2 (10 mol%), DPEphos (20 mol%) Et 3, toluene, 90 C 2. s 4 (14 mol%), M;
Current Literature. Development of Highly Potent and Selective Steroidal Inhibitors and Degraders of CDK8
Current Literature Development of ighly Potent and Selective Steroidal Inhibitors and Degraders of CDK8 ACS Med. Chem. Lett. 2018, ASAP Rational Drug Development simplification Cortistatin A 16-30 steps;
Supporting Information. A Structure-Activity Study of Nickel NNN Pincer Complexes for Alkyl-Alkyl Kumada and Suzuki-Miyaura Coupling Reactions
Supporting Information A Structure-Activity Study of Nickel NNN Pincer Complexes for Alkyl-Alkyl Kumada and Suzuki-Miyaura Coupling Reactions Thomas Di Franco, Marko Stojanovic, Sébastien Keller, Rosario