A concise enantioselective synthesis of the AB ring system of the manzamine alkaloids by ring-closing enyne metathesis

被引：27

作者：

Clark, JS

Townsend, RJ

Blake, AJ

Teat, SJ

Johns, A

机构：

[1] Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England

[2] SERC, Daresbury Lab, CLRC, Warrington WA4 4AD, Cheshire, England

[3] GlaxoSmithKline, Dept Med Chem, Harlow CM19 5AW, Essex, England

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 18期

基金：

英国工程与自然科学研究理事会;

关键词：

manzamine; alkaloids; ring-closing; enyne; metathesis;

D O I：

10.1016/S0040-4039(01)00404-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The AB ring system found in the manzamine A and related alkaloids has been prepared from (-)-quinine by a short enantioselective route. The key step in the sequence is a ruthenium-catalysed ring-closing enyne metathesis re action which delivers a bicyclic diene in good yield. The functionality required for further elaboration of the AB system has been installed by sequential regioselective hydroboration and stereoselective catalytic aminohydroxylation. (C) 2001 Elsevier Science Ltd. AH rights reserved.

引用

页码：3235 / 3238

页数：4

共 56 条

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