Synthesis of harzialactone A and its isomers from D-glucose and assignment of absolute stereochemistry

被引:21
|
作者
Mereyala, HB [1 ]
Joe, M [1 ]
Gadikota, RR [1 ]
机构
[1] Indian Inst Chem Technol, Div Organ Chem 3, Hyderabad 500007, Andhra Pradesh, India
关键词
D O I
10.1016/S0957-4166(00)00389-X
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The synthesis of the marine metabolite (3R,5R)-harzialactone A 1 from D-glucose is described. Syntheses of all the isomers (3S,5R)-2, (3R,5S)-3 and (3S,5S)-4 of 1 are also described and the absolute stereochemistry for the natural product 1 is assigned unambiguously. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:4071 / 4081
页数:11
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