Studies in marine macrolide synthesis: stereocontrolled synthesis of a C21-C34 subunit of the aplyronines

Studies in marine macrolide synthesis: stereocontrolled synthesis of a C21-C34 subunit of the aplyronines
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DOI:
10.1016/s0040-4039(02)01217-0
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发表时间:
2002-08-19
影响因子:
1.8
通讯作者:
Cowden, CJ
Cowden, CJ
中科院分区:
化学4区
文献类型:
--
作者:
Paterson, I;Blakey, SB;Cowden, CJ

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采用β -酮膦酸5与醛19的Horner-Wadsworth-Emmons偶联法制备了aplyronines的C21-C34亚基27,包含8个立体中心和末端n -甲基- n -乙烯基甲酰胺部分。这两个立体四元序列是通过手性酮醛反应构建的,而n -甲基- n -乙烯基甲酰胺则是通过一种新的Wittig烯化反应引入的。(C) 2002 Elsevier Science Ltd.版权所有。
The C21-C34 subunit 27 of the aplyronines, containing eight stereocentres and a terminal N-methyl-N-vinylformamide moiety, was prepared using the Horner-Wadsworth-Emmons coupling of beta-ketophosphonate 5 with aldehyde 19. The two stereotetrad sequences were constructed by chiral ketone aldol reactions, while the N-methyl-N-vinylformamide was introduced using a novel Wittig olefination. (C) 2002 Elsevier Science Ltd. All rights reserved.