Intramolecular S-N(2) ring opening of a cyclic sulfate: Synthesis of erythro-(-)-6-acetoxy-5-hexadecanolide - A major component of mosquito oviposition attractant pheromone

被引：15

作者：

Lohray, BB

Venkateswarlu, S

机构：

[1] Dr. Reddy's Research Foundation, Miyapur, Hyderabad-500050, Bollaram Road

来源：

TETRAHEDRON-ASYMMETRY | 1997年 / 8卷 / 04期

关键词：

D O I：

10.1016/S0957-4166(97)00011-6

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Methyl trans-hexa-5-decenoate is dihydroxylated using AD-mix-alpha followed by treatment with thionyl chloride to furnish cyclic sulfite 8 as the major product. The cyclic sulfite 8 is oxidized to the cyclic sulfate 2. Highly regio- and stereospecific ring opening of (4S, 5S)-carboxybutyl-5-decylcyclic sulfate generated in situ by the hydrolysis of 2 furnished (5R,6S)-6-hydroxy-5-hexadecanolide 9 in high yield. Acetylation of 9 afforded natural oviposition attractant pheromone 1 in good yield. (C) 1997 Elsevier Science Ltd.

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页码：633 / 638

页数：6

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