Scientific article
English

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

Published inHelvetica chimica acta, vol. 64, no. 7, p. 2489-2491
Publication date1981-11-04
First online date2004-10-25
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 12 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.

Citation (ISO format)
VON OPPOLZER, Wolfgang, BÄTTIG, Kurt. A Short and Efficient Synthesis of (±)-Modhephene by a Stereoelectronically-Controlled Ene-Reaction. Preliminary communication. In: Helvetica chimica acta, 1981, vol. 64, n° 7, p. 2489–2491. doi: 10.1002/hlca.19810640756
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Journal ISSN0018-019X
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