Applications of crotonyldiisopinocampheylboranes in synthesis: Total synthesis of restrictinol

被引：25

作者：

Barrett, AGM ^{[1
]}

Bennett, AJ ^{[1
]}

Menzer, S ^{[1
]}

Smith, ML ^{[1
]}

White, AJP ^{[1
]}

Williams, DJ ^{[1
]}

机构：

[1] Univ London Imperial Coll Sci Technol & Med, Dept Chem, London SW7 2AY, England

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1999年 / 64卷 / 01期

关键词：

D O I：

10.1021/jo9815305

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The total synthesis of restrictinol, the hydrolysis product of the antifungal natural product restricticin, starting from commercially available methyl (S)-(+)-3-hydroxy-2-methylpropionate is described. Key stages in the strategy involved (i) the use of Brown's allylboration chemistry to construct an acyclic intermediate bearing three of the four stereogenic centers of the natural product, (ii) formation of a C-glycosidic vinyl iodide, and (iii) introduction of the triene side chain via a Suzuki coupling reaction.

引用

页码：162 / 171

页数：10

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