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.
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收藏
页码：1643 / 1646
页数：4
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