A novel approach for total synthesis of cryptophycins via asymmetric crotylboration protocol

被引：34

作者：

Dhokte, UP ^{[1
]}

Khau, VV ^{[1
]}

Hutchison, DR ^{[1
]}

Martinelli, MJ ^{[1
]}

机构：

[1] Eli Lilly & Co, Lilly Res Labs, Chem Proc R&D, Indianapolis, IN 46285 USA

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 48期

关键词：

D O I：

10.1016/S0040-4039(98)01994-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Acyclic and a highly efficient stereoselective C-C bond formation of aldehyde 3 with the crotylboron reagent 4, derived from (-)-alpha-pinene, provided a homoallylic alcohol 6 in greater than or equal to 99% enantio-(ee) and diastereomeric excess (de). The alcohol 6 was linearly converted into the desired Fragment A 10 of cryptophycins in seven steps. This enantiomerically pure Fragment A was conveniently and efficiently coupled with the other three fragments, namely B, C and D, and provided the desired cryptophycin A derivative (LY404291). The terminal double bond in LY404291 was further elaborated to provide a terminal epoxide LY404292, and cryptophycins 51 and 52. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：8771 / 8774

页数：4

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