Enantioselective formal total synthesis of the antitumor macrolide bryostatin 7

被引：57

作者：

Manaviazar, Soraya ^{[1
]}

Frigerio, Mark ^{[1
]}

Bhatia, Gurpreet S. ^{[1
]}

Hummersone, Marc G. ^{[1
]}

Aliev, Abil E. ^{[1
]}

Hale, Karl J. ^{[1
]}

机构：

[1] UCL, Ctr Chem Genom, Christopher Ingold Labs, Dept Chem, London WC1H 0AJ, England

来源：

ORGANIC LETTERS | 2006年 / 8卷 / 20期

关键词：

D O I：

10.1021/ol061626i

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new enantioselective synthesis of Masamune's AB fragment (1) for bryostatin 7 is described. Key steps in the new route include a Meerwein-Ponndorf -Verley reduction to set the O(7) stereocenter and an alkylative union between the dithiane 6 and iodide 5 to construct the C(9) C(10) bond. Because we have previously published a synthesis of Masamune's C-ring phenyl sulfone 2, our new route to 1 constitutes a formal total synthesis of bryostatin 7; it also corrects the previously reported spectral data for 1 in CDCl3.

引用

页码：4477 / 4480

页数：4

共 50 条

[41] Total synthesis of bryostatin 2
Evans, DA
Carter, PH
Carreira, EM
Charette, AB
Prunet, JA
Lautens, M
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (33) : 7540 - 7552
[42] Total synthesis of bryostatin 3
Trost, Barry M.
Wang, Youliang
Buckl, Andreas K.
Huang, Zhongxing
Nguyen, Minh H.
Kuzmina, Olesya
SCIENCE, 2020, 368 (6494) : 1007 - +
[43] An enantioselective synthesis of the C2-C16 segment of antitumor macrolide laulimalide
Ghosh, AK
Wang, Y
TETRAHEDRON LETTERS, 2000, 41 (14) : 2319 - 2322
[44] Total synthesis of bryostatin 3
Ohmori, Ken
Ogawa, Yasuyuki
Obitsu, Tetsuo
Ishikawa, Yuichi
Nishiyama, Shigeru
Yamamura, Shosuke
Angewandte Chemie (International Edition in English), 2000, 39 (13): : 2290 - 2294
[45] Total synthesis of bryostatin 3
Ohmori, K
Ogawa, Y
Obitsu, T
Ishikawa, Y
Nishiyama, S
Yamamura, S
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2000, 39 (13) : 2290 - 2294
[46] Total Synthesis of Bryostatin 9
Wender, Paul A.
Schrier, Adam J.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (24) : 9228 - 9231
[47] Total and formal enantioselective synthesis of lyngbic acid and hermitamides A and B
Virolleaud, Marie-Alice
Menant, Christine
Fenet, Bernard
Piva, Olivier
TETRAHEDRON LETTERS, 2006, 47 (29) : 5127 - 5130
[48] Enantioselective approaches to aminocyclopentitols: A total synthesis of (+)-6-epitrehazolin and a formal total synthesis of (+)-trehazolin
Li, J
Lang, FR
Ganem, B
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (10): : 3403 - 3410
[49] Enantioselective total synthesis of the proposed structure of macrolide iriomoteolide-1b
Ye, Zhengqing
Gao, Tingyi
Zhao, Gang
TETRAHEDRON, 2011, 67 (33) : 5979 - 5989
[50] Formal total synthesis of (±)-7-deoxypancratistatin
Shukla, Krupa H.
DeShong, Philip
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2009, 238

← 1 2 3 4 5 →