Asymmetric synthesis of the left hand portion of the azinomycins

被引：27

作者：

Bryant, HJ

Dardonville, CY

Hodgkinson, TJ

Hursthouse, MB

Malik, KMA

Shipman, M ^{[1
]}

机构：

[1] Univ Loughborough, Dept Chem, Loughborough LE11 3TU, Leics, England

[2] Univ Exeter, Dept Chem, Exeter EX4 4QD, Devon, England

[3] Univ Wales, Dept Chem, Cardiff CF1 3TB, S Glam, Wales

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1998年 / 07期

关键词：

D O I：

10.1039/a709084f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A nine step synthesis of the left hand portion of the azinomycins is described starting from 3,3-dimethylacrylic acid. The approach relies on a Sharpless asymmetric dihydroxylation (AD) reaction to install the requisite (2S,3S)-stereochemistry of epoxy alcohol 4. This epoxide is converted to crystalline amide derivative 12 whose structure and absolute stereochemistry have been unambiguously established using X-ray crystallography, Coupling of epoxy alcohol (2S,3S)-4 with naphthoyl chloride 16 and subsequent manipulations furnish epoxy amide (2S,3S)-1 identical in all respects with the natural material.

引用

页码：1249 / 1255

页数：7

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