The synthesis of (-)-cis- and (-)-trans-crobarbatic acid

被引：18

作者：

Donohoe, TJ

Stevenson, CA

Helliwell, M

Irshad, R

Ladduwahetty, T

机构：

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

[2] Merck Sharp & Dohme Ltd, Neurosci Res Ctr, Harlow CM20 2QR, Essex, England

来源：

TETRAHEDRON-ASYMMETRY | 1999年 / 10卷 / 07期

基金：

英国工程与自然科学研究理事会;

关键词：

D O I：

10.1016/S0957-4166(99)00097-X

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The synthesis of both cis- and trans-crobarbatic acid is reported. The five-step sequence proceeds in high yield and with control of both relative and absolute stereochemistry. The key step in the synthesis is the Birch reductive alkylation of a chiral furoic acid which sets the absolute stereochemistry of the products. The stereochemistry of the compounds described was proven unambiguously by X-ray crystallography on one synthetic intermediate and on trans-crobarbatic acid. (C) 1999 Elsevier Science Ltd, All rights reserved.

引用

页码：1315 / 1322

页数：8

共 14 条

[1]

Adams R, 1939, J AM CHEM SOC, V61, P2815

[2] THE ALKALOIDS OF SENECIO-JACOBAEA L .4. THE STRUCTURES OF JACOBINE, JACONINE, JACOLINE AND THEIR CONSTITUENT ACIDS [J].