What is amphidinolide V?: Report on a likely conquest

被引:68
作者
Fuerstner, Alois [1 ]
Larionov, Oleg [1 ]
Fluegge, Susanne [1 ]
机构
[1] Max Planck Inst Kohlenforsch, D-45470 Mulheim, Germany
关键词
alkynes; macrolides; metathesis; natural products; structure elucidation;
D O I
10.1002/anie.200701640
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) The awesome power of metathesis is reflected in the synthesis of the proposed structure of the cytotoxic natural product amphidinolide V, as well as of all other stereomers containing a trans-epoxide unit. It can be concluded from the comprehensive data set obtained that the 8S,9R,10R,13S-configured compound 1 most likely represents amphidinolide V, even though a single resonance in the 1H NMR spectrum deviates from the reported value. © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:5545 / 5548
页数:4
相关论文
共 56 条
[1]   Total syntheses of amphidinolide T1, T3, T4, and T5 [J].
Aïssa, C ;
Riveiros, R ;
Ragot, J ;
Fürstner, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (50) :15512-15520
[2]  
[Anonymous], 2005, ANGEW CHEM
[3]   The modified Julia olefination:: alkene synthesis via the condensation of metallated heteroarylalkylsulfones with carbonyl compounds [J].
Blakemore, PR .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, (23) :2563-2585
[4]   A comparative analysis of the total syntheses of the amphidinolide T natural products [J].
Colby, EA ;
Jamison, TF .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2005, 3 (15) :2675-2684
[5]   Total syntheses of amphidinolides T1 and T4 via catalytic, stereoselective, reductive macrocyclizations [J].
Colby, EA ;
O'Brien, KC ;
Jamison, TF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (12) :4297-4307
[6]   Stereocontrolled and convergent total synthesis of amphidinolide T3 [J].
Deng, Li-Sheng ;
Huang, Xiao-Ping ;
Zhao, Gang .
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (12) :4625-4635
[7]   Enyne metathesis (enyne bond reorganization) [J].
Diver, ST ;
Giessert, AJ .
CHEMICAL REVIEWS, 2004, 104 (03) :1317-1382
[8]   Total syntheses of the actin-binding macrolides latrunculin A, B, C, M, S and 16-epi-latrunculin B [J].
Fuerstner, Alois ;
De Souza, Dominic ;
Turet, Laurent ;
Fenster, Michael D. B. ;
Parra-Rapado, Liliana ;
Wirtz, Conny ;
Mynott, Richard ;
Lehmann, Christian W. .
CHEMISTRY-A EUROPEAN JOURNAL, 2007, 13 (01) :115-134
[9]   Latrunculin analogues with improved biological profiles by "diverted total synthesis":: Preparation, evaluation, and computational analysis [J].
Fuerstner, Alois ;
Kirk, Douglas ;
Fenster, Michaeel B. ;
Aissa, Christophe ;
De Souza, Dominic ;
Nevado, Cristina ;
Tuttle, Tell ;
Thiel, Walter ;
Mueller, Oliver .
CHEMISTRY-A EUROPEAN JOURNAL, 2007, 13 (01) :135-149
[10]   Total synthesis of Iejimalide B [J].
Fuerstner, Alois ;
Nevado, Cristina ;
Tremblay, Martin ;
Chevrier, Carine ;
Teply, Filip ;
Aissa, Christophe ;
Waser, Mario .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (35) :5837-5842