Convergent Route to ent-kaurane Diterpenoids: Total Synthesis of Lungshengenin D and 1α6α- Diacetoxy-ent-kaura-9(11),16-dien- 12,15-dione
|
|
|
- Nancy Patience Owen
- 5 years ago
- Views:
Transcription
1 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 of rganic Chemistry, Chinese Academy of Sciences February 10, 2017 Presented by: Chris Peruzzi Ac J. Am. Chem. Soc. 2017, 139 (8),
2 Ent-kaurane Diterpenoids Discovered in 1961 in Kauri trees of ew Zealand >1000 ent-kauranes isolated Preliminary studies show anti-tumor, anti-infective and immunosuppressive properties of these natural products ent-kaurane
3 Retrosynthetic Analysis Ac Lungshengenin D Ac Mukaiyama- Michael-type reaction Cb Ac Cb = C( i Pr) 2 omoaldol reaction Cb Et Et A C B TBDPS TBDPS TBDPS
4 Retrosynthetic Analysis A B TMS LA TMS 2 R 1 R 2 R 2 R 1 R 2 R 1
5 Retrosynthetic Analysis Ac Lungshengenin D Ac Mukaiyama- Michael-type reaction Cb Ac Cb = C( i Pr) 2 omoaldol reaction Cb Et Et A C B TBDPS TBDPS TBDPS
6 Making Synthon A CBS Catalyst Ph Ph B $2.36/gram 1.5 equiv $0.06/gram 7 mol% 2 S 4 neat, reflux, 18 h 63% multi-gram scale 0.5 equiv CBS Catalyst 1.1 equiv B 3 TF complex toluene, 40 C, 10 h, 90% 99% ee 1.5 equiv a TF, reflux, 1 h then 1.4 equiv ClC( i Pr) 2 TF, reflux, 12 h, 85% Cb Paquette, L. A.; plinger, J. A. Tetrahedron. 1989, 45 (1),
![Making Synthon B Et $4.59/gram Et TBDPS 2.5 equiv [(C3)2C] 2 Li, TF, 78 C, 1 h then 1.3 equiv Cl 78 C, 30 min rt, 4 h 1.](/docs-images/94/122229964/images/7-0.jpg "4 equiv [(C3)2CC 2]2 Al toluene, 20 C, 4 h then 5% Cl,, rt, 12 h, 78% 2.5 equiv IC 2 C 2 TBDPS 2.")
7 Making Synthon B Et $4.59/gram Et TBDPS 2.5 equiv [(C3)2C] 2 Li, TF, 78 C, 1 h then 1.3 equiv Cl 78 C, 30 min rt, 4 h 1.4 equiv [(C3)2CC 2]2 Al toluene, 20 C, 4 h then 5% Cl,, rt, 12 h, 78% 2.5 equiv IC 2 C 2 TBDPS 2.0 equiv Cs 2 C 3 C 3 C, 65 C, 12 h, 65% TBDPS Et TBDPS 2.5 equiv CF 3 S 3Si(C3)2C(C3)3 4.0 equiv Et 3 TF, 60 C 5 mol% Pd 2(dba) mol% (S) -t Bu-Phox TF, 40 C, 24 h, 82% 0.1 equiv Pd(Ac)2 2 balloon 2 S, 40 C, 6 h 82% Et TBDPS 87% ee TBDPS dba (S)- t Bu-Phox P Ph Ph
![Making Synthon B Et TBDPS 1.4 equiv [(C3)2CC 2]2 Al toluene, 20 C, 4 h then 5% Cl,, rt, 12 h, 78% TBDPS 2.5 equiv CF 3 S 3Si(C3)2C(C3)3 4.0 equiv Et 3 TF, 60 C 0.](/docs-images/94/122229964/images/8-0.jpg "1 equiv Pd(Ac)2 2 balloon 2 S, 40 C, 6 h 82% TBDPS TBDPS 15 equiv (C2) 2 0.1 equiv PPTs benzene, reflux, 24 h 90% TBDPS 1.25 equiv TBAF TF, 0 C to rt, 2 h 0.1 equiv TPAP 1.")
8 Making Synthon B Et TBDPS 1.4 equiv [(C3)2CC 2]2 Al toluene, 20 C, 4 h then 5% Cl,, rt, 12 h, 78% TBDPS 2.5 equiv CF 3 S 3Si(C3)2C(C3)3 4.0 equiv Et 3 TF, 60 C 0.1 equiv Pd(Ac)2 2 balloon 2 S, 40 C, 6 h 82% TBDPS TBDPS 15 equiv (C2) equiv PPTs benzene, reflux, 24 h 90% TBDPS 1.25 equiv TBAF TF, 0 C to rt, 2 h 0.1 equiv TPAP 1.5 equiv M C 2 Cl 2, 0 C to rt, 2 h 58% C PPTs S 3 - M TPAP Ru
9 C Cb R Li oppe's omoaldol 1.63 equiv s -BuLi 1.63 equiv rac-tmcda Et 2, 78 C to rt, 8 h 10.0 equiv Ac equiv DMAP C 2 Cl 2, 0 C to rt, 4 h 82% gram scale rac-tmcda 2 Cb Ac dr = 1.3:1 DMAP 2 2 ( i Pr) 2 Mukaiyama-Michael type reaction Cb Ac 1.0 equiv BF 3 Et 2 C 2 Cl 2, 78 C to 20 C, 4 h then, ac 3 workup, 80% Ac Ac 67%, dr = 1.3:1 13%, dr = 1.3:1 Ac Cb LA
10 Finishing the Core Structure Ac 6.0 equiv K 2 C 3, reflux, 4 h 1.3 equiv IBX 2 S, 3 h, rt 93% 15.0 equiv TF, reflux, 12 h, 85% 3.0 equiv K(Si3)2 TF, 78 C, 1 h 3.0 equiv TBSCl TF, 0 C, 1 h TBS TBS 4.0 equiv DDQ 8.0 equiv DTBMP C 3 C, rt, 48 h then 2 Cl, 0 C to rt 65% 1.2 equiv t BuK TF, 78 C to 40 C, 1 h 1.2 equiv (PhSe)2 TF, rt to 40 C, 48 h 40% 2 Cl /TF, 50 C, 12 h, 82% Cl Cl DDQ C C t Bu DTBMP t Bu IBX I
11 1.0 equiv ab 4 Et/C 2 Cl 2, 30 C to 10 C, 2 h 55% 1.0 equiv DMAP 10.0 equiv Et equiv MsCl C 2 Cl 2, 0 C to rt, 2 h 100% Ms Ms 12.0 equiv LiAl 4 TF, 0 C to reflux, 6 h 4.6 equiv IBX 2 S, 60 C, 3 h, 75% 12.0 equiv t Bu 3.0 equiv Bz 3 + TF, 0 C, 2 h, 95% 5.0 equiv (PhSe) equiv ab 4 Et, Ac, 0 C to rt, 1.5 h 85% 5.0 equiv 4B(Ac)3 Ac/C 3 C, 0 C to rt, 2 h 87% 1.0 equiv DMAP 10.0 equiv pyridine 2.0 equiv Ac 2 C 2 Cl 2, 0 C, 2 h, 69% Ac Lungshengenin D
12 CBS Catalytic Cycle
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
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
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
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
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
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 (+)-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
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
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.
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
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
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,
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
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,
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,
Initials: 1. Chem 633: Advanced Organic Chemistry 2011 Final Exam
Initials: 1 ame: Chem 633: Advanced rganic Chemistry 2011 Final Exam Please answer the following questions clearly and concisely. In general, use pictures and less than 10 words in your answers. Write
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
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,
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
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
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.
Keisuke Suzuki. Baran lab Group Meeting 6/11/16. Shigenobu Umemiya. Akira Suzuki. Takanori Suzuki (Hokkaido University)
197.D., Teruaki Mukaiyama, University of Tokyo 193 Assistant Professor, Keio University 197 Lecturer, Keio University 199 Assocate Professor, Keio University 1990 Visiting Professor, ET 1994 ull Professor,
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 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
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
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
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
Synthetic Methodology. Using Tertiary Phosphines. as Nucleophilic Catalysts
Synthetic Methodology Using Tertiary osphines as Nucleophilic Catalysts 1 3 2 u 2 (P 3 ) 3 4 1 2 D. Ma, X. Lu 1988 1 2 Pd 2 (dba) 3.CCl 3 /P 3 /Ac or Pd(Ac) 2 /P 3 1 2 B. M. Trost 1988 1 3 2 u 2 (P 3 )
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.
Functionalization of C(sp 3 ) H Bonds Using a Transient Directing Group
Literature eport Functionalization of C(sp 3 ) Bonds Using a Transient Directing Group eporter: Mu-Wang Chen Checker: Yue Ji Date: 2016-04-05 Yu, J.-Q. et al. Science 2016, 351, 252-256. Scripps esearch
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
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
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
Chapter 5 Three and Four-Membered Ring Systems
Chapter 5 Three and Four-mbered ing ystems 5.1 Aziridines Aziridines are good alkylating agents because of their tendency to undergo ring-opening reaction with nucleophiles 例 mitomycin C antibiotic and
CEM 852 Exam What is the ratio of (S) / (R) alcohol formed during this reaction? (2 pts) baker's yeast. H 2 O, sucrose 25 C
CEM 852 Exam-1 February 19, 2005 This exam consists of 5 pages. Please write ALL your answers in the answer books. Please write legibly and draw all structures clearly. Good luck. 1. What is the ratio
H H H OH OH H OH H O 1 CH 2 OH
Name 215 F07-Exam No. 3 Page 2 I. (29 points) Streptomycetes are soil-dwelling, filamentous, Gram-positive saprophytic bacteria. They are responsible for over 50% of the known microbial metabolites, including
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
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
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,
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
Literature Report 3. Rapid Syntheses of (+)-Limaspermidine and (+)-Kopsihainanine A. Date :
Literature Report 3 Rapid Syntheses of (+)-Limaspermidine and (+)-Kopsihainanine A Reporter : Xiao-Yong Zhai Checker : Shubo u Date : 2017-10-30 Pritchett, B. P.; Donckele, E. J.; Stoltz, B. M. Angew.
C-O C-O C-N A A. (KHMDS) C-N (scheme 1) C-O C-N (1)
C- C- C- A A 2007 2008 -t- (Boc)-- (MM)- () (KMDS) C- (scheme ) C- C- () C- C- C- C- C- C- B C- B (scheme 2) C- B (2) C- manzacidin A Manzacidine A (5) - ATP (fig. ) C- 5 Ph MM Boc ethyl lactate X n=,2
Enantioselective Total Synthesis of (-)-Acetylaranotin, a Dihydrooxepine Epidithiodiketopiperazine
Enantioselective Total Synthesis of (-)-Acetylaranotin, a Dihydrooxepine Epidithiodiketopiperazine Julian A. Codelli, Angela L. A. Puchlopek, and Sarah E. Reisman* JACS. ASAP. ct. 24, 2011 DI: 10.1021/ja209354e
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,
Silenes in organic synthesis: a concise synthesis of (±)-epi-picropodophyllin
lenes in organic synthesis: a concise synthesis of (±)-epi-picropodophyllin obert D. C. Pullin, Jonathan D. Sellars, and Patrick G. Steel* rg. Biomol. Chem., 2007, 5, 3201-3206 H H C Adam Hoye Current
CHEM 330. Final Exam December 5, 2014 ANSWERS. This a closed-notes, closed-book exam. The use of molecular models is allowed
CEM 330 Final Exam December 5, 2014 Your name: ASWERS This a closed-notes, closed-book exam The use of molecular models is allowed This exam consists of 12 pages Time: 2h 30 min 1. / 30 2. / 30 3. / 30
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.
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
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
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
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
Chiral Proton Catalysis in Organic Synthesis. Samantha M. Frawley Organic Seminar September 14 th, 2005
Chiral Proton Catalysis in rganic Synthesis Samantha M. Frawley rganic Seminar September 14 th, 2005 Seminar utline Introduction Lewis Acid-assisted Chiral Brønsted Acids Enantioselective protonation for
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)
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,
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 Atisine-type Alkaloids
Literature Report III Synthesis of Atisine-type Alkaloids Reporter : Yang Zhao Checker : Zhou-ao Zhu Date : 2018-7-16 Ma, D. et al. Angew. Chem. Int. Ed. 2018, 57, 6676 Baran, P. S. et al. J. Am. Chem.
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
[3,3]-Sigmatropic rearrangements
![[3,3]-Sigmatropic rearrangements](/thumbs/75/71504906.jpg "[3,3]-Sigmatropic rearrangements")
1 [3,3]-Sigmatropic rearrangements heat R 1 R 3 R 1 R 3 R 1 R 3 A class of pericyclic reactions whose stereochemical outcome is governed by the geometric requirements of the cyclic transition state Reactions
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.
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
ROC Exam Problem 1
RC Exam 2012 Problem 1 Silyl ether 1 is transformed into 2 in a two step process. Predict, through a detailed mechanistic rationale, the stereochemistry of the newly formed chiral center. TBS Si 1) Ms
Recent Total Syntheses! Published in Nature!
Recent Total Syntheses! Published in ature! Eric ewcomb 8/21/2011! 2 S 3 2 2 ature Then and ow! First published ov. 4th, 1869 First issue states two objectives: 'The objective which it is proposed to attain
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
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
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
Supporting Information. The synthesis of cardenolide and bufadienolide aglycones, and related steroids bearing a. heterocyclic subunit
Electronic upplementary Material (EI) for Natural Product eports. This journal is The oyal ociety of Chemistry 2017 upporting Information The synthesis of cardenolide and bufadienolide aglycones, and related
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
Synthesis of the HCV Protease Inhibitor Vaniprevir (MK- 7009) Using Ring-Closing Metathesis Strategy
ynthesis of the CV Protease Inhibitor Vaniprevir (MK- 7009) Using Ring-osing Metathesis trategy Jongrock Kong*, Cheng-yi Chen*, Jaume Balsells-Padros, Yang Cao, Robert F. Dunn, arah J. Dolman, Jacob Janey,
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
Catalytic Asymmetric [4+1] Annulation of Sulfur Ylides with Copper Allenylidene Intermediates. Reporter: Jie Wang Checker: Shubo Hu Date: 2016/08/02
![Catalytic Asymmetric [4+1] Annulation of Sulfur Ylides with Copper Allenylidene Intermediates. Reporter: Jie Wang Checker: Shubo Hu Date: 2016/08/02](/thumbs/93/114018431.jpg "Catalytic Asymmetric [4+1] Annulation of Sulfur Ylides with Copper Allenylidene Intermediates. Reporter: Jie Wang Checker: Shubo Hu Date: 2016/08/02")
Catalytic Asymmetric [4+1] Annulation of Sulfur Ylides with Copper Allenylidene Intermediates Reporter: Jie Wang Checker: Shubo Hu Date: 2016/08/02 Xiao, W.-J. et al. J. Am. Chem. Soc. 2016, 138, 8360.
Enantioselective Synthesis of Pactamycin, a Complex Antitumor Antibiotic
Journal Club (3) Tomoya akamura Enantioselective Synthesis of Pactamycin, a Complex Antitumor Antibiotic Justin T. Malinowski, Robert J. Sharpe, Jeffrey S. Johnson Science 03, 30, 80 8.. Introduction -.
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
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.
!"#$%&&'!&(!)*+,-./!01"2.3$*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
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 (-)-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.
"-Amino Acids: Function and Synthesis
"-Amino Acids: Function and Synthesis # Conformations of "-Peptides # Biological Significance # Asymmetric Synthesis Sean Brown MacMillan Group eting ovember 14, 2001 Lead eferences: Cheng,. P.; Gellman,
Mechanism Problem. 1. NaH allyl bromide, THF N H
Mechanism Problem 1. a allyl bromide, TF 2. 9-BB (1.2 equiv), TF, rt; ame (1.2 equiv); t-buli (2.4 equiv), TMEDA (2.4 equiv) 30 to rt; allyl bromide; 30% 2 2, aq. a, 0 C (58% yield) Mechanism Problem 9-BB
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.
Branched-Regioselective Hydroformylation with Catalytic Amounts of a Reversibly Bound Directing Group
1/12 Branched-egioselective ydroformylation with Catalytic Amounts of a eversibly Bound Directing Group h(i)/me C/ 2 MS 4A branched major by Christian U. Grünanger and Bernhard Breit Angew. Chem. Int.
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
Towards a Total Synthesis of Anatoxin-a(s)
Towards a Total Synthesis of Anatoxin-a(s) 2 P Me Me 2 Eric E. Buck Research Topic Seminar September 19, 2009 Eric Buck @ Wipf Group Page 1 of 27 10/3/2009 Background Anatoxin-a(s) is a neurotoxin produced
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
Asymmetric Lewis Base Strategies for Heterocycle Synthesis
Asymmetric Lewis Base trategies for eterocycle ynthesis Dr Andrew mith EatCEM, chool of Chemistry, University of t Andrews 1st cottish-japanese ymposium of rganic Chemistry, University of Glasgow Friday
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
Catalytic Reactions in Organic Synthesis
17 April, 2008 Catalytic eactions in rganic Synthesis hodium Complexes and edox Catalysts Koichi AASAKA, Motoki YAMAE, Shunsuke CIBA Division of Chemistry and Biological Chemistry, School of ysical and
Exam 2 - Key Unless otherwise indicated, clearly indicate stereochemistry. You may use molecular models.
Exam 2 - Key Unless otherwise indicated, clearly indicate stereochemistry. You may use molecular models. 1. (16 pts) For each of the following hypothetical equilibration reactions 1 below, write the pk
Highly Cytotoxic, Structure Similar Polyke>des CO 2 H
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,
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'
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
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
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
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,
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
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
Introduction to Synthesis: Design (CHE686) Spring 2015 Exam #1 3/6/15
Introduction to ynthesis: Design (CE686) pring 2015 Exam #1 3/6/15 AME: KEY ome Pointers: 1. ELAX!! 2. ead the instructions for each question carefully. Be sure you understand what is required. If you
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
Cladiellin, Briarellin, Asbestinin & Sarcodictyin Diterpenes
Cladiellin, Briarellin, Asbestinin & Sarcodictyin Diterpenes I. Introduction Cembranes are a large class of macrocyclic diterpenes (C 20) isolated from a diverse group of organisms (both plants and animals)