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Total Synthesis of (±)-Silphinene: non photochemical cyclobutenic route to a crucial intermediate

✍ Scribed by Michel Miesch; Laurence Miesch-Gross; Michel Franck-Neumann

Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
432 KB
Volume
53
Category
Article
ISSN
0040-4020

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✦ Synopsis

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, an aUylic oxidation stereospecifically introduces a hydroxyl group at position 8. Following formation of the benzyl ether, the diquinane 9 was then Ixansformed in four steps into the triquinane 20 using a silyl-assisted Nazarov type cyclisation, From this intermediate, (+)-silphinene has previously been synthesized.

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