Total synthesis of rhizoxin D

被引：11

作者：

N'Zoutani, MA ^{[1
]}

Lensen, N ^{[1
]}

Pancrazi, A ^{[1
]}

Ardisson, J ^{[1
]}

机构：

[1] ESCOM, UCP, CNRS, UMR 8123,Lab Synth Organ Select & Chim Organomet, F-95092 Cergy Pontoise, France

来源：

SYNLETT | 2005年 / 03期

关键词：

rhizoxin D; total synthesis; Heck cross-coupling; vinyllithium reagents; macrolactonisation;

D O I：

10.1055/s-2005-832373

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A total synthesis of rhizoxin D (1b), a 16-membered antitumoral macrolide, is reported. The strategy relies on the application of a Brown allylation reaction for the C 15 and C16 asymmetric centres control. Installation of the C17 hydroxyl function with concomitant building of the (E)-C18-C19 double bond was effected by a diastereoselective addition of vinyllithium derivative 15 to aldehyde 10. The terminal enone group was then introduced to achieve the preparation of C11-C20 segment 23. A Heck coupling reaction between C11-C20 fragment 23 and C3-C10 segment 24 (previously prepared in our laboratory) was performed with success to deliver the C3-C20 fragment 25. The total synthesis of rhizoxin D (1b) was achieved after transformation of 25 into the macro-lactone 28, and coupling the C21-C28 side chain using a Wittig-Wadsworth-Emmons reaction.

引用

页码：491 / 495

页数：5

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