Synthesis of the tricyclic portions of batzelladines A, B and D. Revision of the stereochemistry of batzelladines A and D

被引：257

作者：

Snider, BB ^{[1
]}

Chen, JS ^{[1
]}

Patil, AD ^{[1
]}

Freyer, AJ ^{[1
]}

机构：

[1] SMITHKLINE BEECHAM PHARMACEUT,DEPT BIOMOL DISCOVERY,DEPT ANALYT SCI,KING OF PRUSSIA,PA 19406

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 39期

基金：

美国国家卫生研究院;

关键词：

D O I：

10.1016/0040-4039(96)01575-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The tricyclic portion 4 of batzelladine B (2) is obtained from 10a, which differs in one side chain from the ptitomycalin A model 10c that we prepared several years ago, by reduction with NaBH3CN in buffered MeOH. Hydrogenation of 11b over Rh/Al2O3 at 50 PSI H-2 affords the proposed tricyclic portion 12b of batzelladine A (1). Epimerization of 12b and hydrolysis affords acid 3, which is similar to, but different from, the acid obtained from hydrolysis of 1. A five step sequence converts 7b to the anti tricyclic acid 15, which is identical to the hydrolysis product of 1. The stereochemistry of the hydrolysis product 15 was confirmed by NOE experiments. Copyright (C) 1996 Elsevier Science Ltd

引用

页码：6977 / 6980

页数：4

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