The total synthesis of the diepoxycyclohexanone antibiotic aranorosin and novel synthetic analogues

被引：41

作者：

McKillop, A ^{[1
]}

McLaren, L ^{[1
]}

Taylor, RJK ^{[1
]}

Watson, RJ ^{[1
]}

Lewis, NJ ^{[1
]}

机构：

[1] SMITHKLINE BEECHAM PHARMACEUT,TONBRIDGE TN11 9AN,KENT,ENGLAND

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1996年 / 12期

关键词：

D O I：

10.1039/p19960001385

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A short synthesis of the novel antibiotic aranorosin in chiral form is described which employs (i) a novel hypervalent iodine-mediated oxidative hydroxylation of a tyrosinal derivative and (ii) a stereocontrolled cis-bisepoxidation in the key steps. A similar procedure was employed to prepare 6'-epiaranorosin, and hence establish the stereochemistry of the natural compound, and to prepare novel aranorosin analogues. An organometallic route is described which gives desamidoaranorosin.

引用

页码：1385 / 1393

页数：9

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