SYNTHESIS OF CIS-FUSED BICYCLIC SYSTEMS BY RADICAL CYCLIZATION APPROACH: FORMAL SYNTHESIS OF ETHISOLIDE AND ISO-AVENACIOLIDE

被引：3

作者：

Sharma, Gangavaram V. M. ^{[1
]}

Chary, Devoju Harinada ^{[1
]}

机构：

[1] CSIR Indian Inst Chem Technol, Organ & Biomol Chem Div, Hyderabad 500007, Andhra Pradesh, India

来源：

SYNTHETIC COMMUNICATIONS | 2014年 / 44卷 / 12期

关键词：

Carbohydrates; 5-exo-dig; exo-methylene; furanoid glycal; radical cyclization; DIVERSITY-ORIENTED SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; ABSOLUTE STEREOCHEMISTRY; 1ST SYNTHESIS; (-)-ISOAVENACIOLIDE; ENANTIOMERS; LACTONES; ROUTE; ACIDS;

D O I：

10.1080/00397911.2013.871562

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Formal synthesis of ethisolide and iso-avenaciolide was achieved using furanoid glycal-vinyl radical intermediates. The vinyl radical cyclization by 5-exo-dig mode gave the cis-fused bicyclic systems with an efficient introduction of the exo-methylene group, besides helping in the inversion of the adjacent stereocentre. Further, the study describes the synthesis of cis-fused bicyclic systems from L-arabinose and D-xylose for the creation of diverse natural and synthetic products of this class.

引用

页码：1771 / 1779

页数：9

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