Approaches to phomactin A: unexpected late-stage observations

被引：8

作者：

Burnell, Erica S. ^{[1
]}

Irshad, Abdur-Rehman ^{[1
]}

Raftery, James ^{[1
]}

Thomas, Eric J. ^{[1
]}

机构：

[1] Univ Manchester, Sch Chem, Manchester M13 9PL, Lancs, England

来源：

TETRAHEDRON LETTERS | 2015年 / 56卷 / 23期

关键词：

Natural products; Diastereoselectivity; Epoxide cleavage; TPAP oxidation; Macrocyclisation; TETRAPROPYLAMMONIUM PERRUTHENATE; TRICYCLIC FURANOCHROMAN; MAGNESIUM BROMIDE; ALCOHOLS; MILD; REARRANGEMENTS; ANTAGONIST; PRECURSORS; OXIDANT; CORE;

D O I：

10.1016/j.tetlet.2015.01.082

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A dihydroxyepoxide analogous to that proposed as a late intermediate in the biosynthesis of phomactin A was prepared by reduction of the corresponding ketoaldehyde. The structure of the dihydroxyepoxide, specifically its configuration at C14, was confirmed by the X-ray crystal structure of its diacetate. The stereoselectivity of reduction of the ketoaldehyde would appear to be influenced by the presence of a remote phenylsulphonyl moiety at C10. Of interest in the context of the biosynthesis of phomactin A was the observation that this dihydroxyepoxide did not rearrange into the isomeric hydroxytetrahydropyran despite having the configuration at C14 required for this rearrangement. (C) 2015 Elsevier Ltd. All rights reserved.

引用

页码：3255 / 3258

页数：4

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