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A Short and Efficient Synthesis of (±)-Modhephene by a Stereoelectronically-Controlled Ene-Reaction

✍ Scribed by Wolfgang Oppolzer; Kurt Bättig

Book ID
102250650
Publisher
John Wiley and Sons
Year
1981
Tongue
German
Weight
162 KB
Volume
64
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

(±)‐Modhephene (6) has been synthesized from the easily available trimethylpentalenone 1 in 6 steps in 26% overall yield (Scheme 2). The remarkably smooth 1,4‐addition/enolate trapping 1 → 2 and subsequent selenoxide elimination after oxidation furnished the key intermediate 3 which underwent an expedient and highly stereoselctive intramolecular ene‐reaction to give the propellane 4, readily convertible to (±)‐6.

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