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Total synthesis of (±)-silphinene

✍ Scribed by Tetsuto Tsunoda; Mitsuaki Kodama; Shô Itô

Book ID
104216867
Publisher
Elsevier Science
Year
1983
Tongue
French
Weight
206 KB
Volume
24
Category
Article
ISSN
0040-4039

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✦ Synopsis

The regio-and stereoselective total synthesis of (+)-silphinene, an angular tricyclopentanoid sesquiterpene, was achieved starting from dicyclopentadiene. Recently sesquiterpenes having a carbon skeleton of three angularly-fused cyclopentanes have attracted

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The cyclobutenic ester 1, readily available by thermal [2+2] cycloaddition of the silyl enol ether derived from cyclopentanone with ethyl propynoate, is easily transformed into the diquinanic alcohol 3 via the bicyclo [2.1.0] pentane intermediate 2. After protection as the thexyldimethylsilyl ether,