Preparation of ginkgolide and F-seco-ginkgolide lactols:: the unique reactivity of α-hydroxy lactones toward NaBH4

被引：11

作者：

Tanaka, K ^{[1
]}

Kester, KD ^{[1
]}

Berova, N ^{[1
]}

Nakanishi, K ^{[1
]}

机构：

[1] Columbia Univ, Dept Chem, New York, NY 10027 USA

来源：

TETRAHEDRON LETTERS | 2005年 / 46卷 / 03期

基金：

美国国家卫生研究院; 日本学术振兴会;

关键词：

ginkgolide; F-seco-siinkaolide; NaBH4; lactone; lactol;

D O I：

10.1016/j.tetlet.2004.10.113

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

It has been found that NaBH4 smoothly reduces the alpha-hydroxy-lactone moieties in ginkgolide and F-seco-ginkgolides to lactols. The reaction is rapid and stops at the lactol stage: the coordination of NNaBH4 to the conformationally rigid cage structure is involved in both the initiation and termination stages. This facile reduction of ginkgolide lactones yield a variety of new ginkgolide lactols. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：531 / 534

页数：4

共 36 条

[1] FLUOROCARBOHYDRATES .6. SELECTIVE REDUCTION OF OXO-ESTERS BY POTASSIUM BOROHYDRIDE [J].