Diastereoselective synthesis of syn-alkanetriols from a glyceral derivative via K-selectride reduction:: Application to the synthesis of a pheromone of the sugarcane weevils

被引：21

作者：

Dhotare, B ^{[1
]}

Salaskar, A ^{[1
]}

Chattopadhyay, A ^{[1
]}

机构：

[1] Bhabha Atom Res Ctr, Div Bioorgan, Bombay 400085, Maharashtra, India

来源：

SYNTHESIS-STUTTGART | 2003年 / 16期

关键词：

K-selectride; reduction; syn-alkanetriols; selectivity; Felkin-Anh model;

D O I：

10.1055/s-2003-42422

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

kappa-selectride reduction of commercially available D-mannitol derived ketones 2b-i produced the corresponding alcohols 3b-i in good yields and with absolute syn-selectivity in almost all the cases. It was proposed that the bulky cyclohexylidene moiety of 3 has a significant role in favoring the reduction with kappa-selectride via Felkin-Anh model. Subsequently, one of the reduction product 3c has been exploited to synthesize the pheromone I of sugarcane weevil.

引用

页码：2571 / 2575

页数：5

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