REDUCTIVE ELIMINATION OF ACETONIDES, CYCLIC CARBONATES, OR CYCLIC SULFITES OF GAMMA,DELTA-DIHYDROXY (E)-ALPHA,BETA-UNSATURATED ESTERS - AN EFFICIENT ROUTE TO DELTA-HYDROXY (E)-BETA,GAMMA-UNSATURATED ESTERS AND DELTA-HYDROXY ESTERS

被引：27

作者：

KANG, SK ^{[1
]}

KIM, SG ^{[1
]}

PARK, DC ^{[1
]}

LEE, JS ^{[1
]}

YOO, WJ ^{[1
]}

PAK, CS ^{[1
]}

机构：

[1] KOREA RES INST CHEM TECHNOL, DAE DEOG DANJI, SOUTH KOREA

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1993年 / 01期

关键词：

D O I：

10.1039/p19930000009

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The acetonides, cyclic carbonates, or cyclic sulfites of gamma,delta-dihydroxy (E)-alpha,beta-unsaturated esters have been found to undergo facile reductive cleavage with samarium diiodide or magnesium in methanol to provide delta-hydroxy (E)-beta,gamma-unsaturated esters or delta-hydroxy esters, respectively. Using the delta-hydroxy ester 3b as a chiral synthon, (-)-5-hexadecanolide, the pheromone of the oriental hornet Vespa orientalis was synthesized.

引用

页码：9 / 10

页数：2

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