Towards a total synthesis of ustiloxins A & B. Stereocontrolled synthesis of (2S,4S,6S)-4-hydroxy-5-phenylsulfinylnorvaline

被引：40
|
作者：
Hutton, CA
White, JM
机构：
[1] School of Chemistry, University of Melbourne, Parkville
来源：
TETRAHEDRON LETTERS | 1997年 / 38卷 / 09期
关键词：
D O I：
10.1016/S0040-4039(97)00110-X
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A short, stereocontrolled synthesis of (2S,4S,6S)-4-hydroxy-5-phenylsulfinylnorvaline (8), an unusual amino acid component of ustiloxins A & B, has been achieved. Stereoselective bromolactonisation of N-Boc-(S)-allylglycine (3) is followed by substitution of the bromide 4a with thiophenol to give the corresponding sulfide 5. Highly stereoselective oxidation of the sulfide 5 gives the corresponding sulfoxide 6a. Removal of the Boc group and lactone ring opening then complete the synthesis of the unusual amino acid. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码：1643 / 1646
页数：4
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