Syntheses of (±)??and Enantiomerically Pure (+)??Longifolene and of (±)??and Enantiomerically Pure (+)??Sativene by an Intramolecular de Mayo Reaction

W Oppolzer, T Godel

Index: Oppolzer, Wolfgang; Godel, Thierry Helvetica Chimica Acta, 1984 , vol. 67, p. 1154 - 1167

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Citation Number: 31

Abstract

Abstract Starting from 2-cyclopentenoyl chloride ((RS)-or (S)-8), the racemic as well as the enantiomerically pure (+)-sesquiterpenes longifolene ((±)-and (+)-1, resp.) and sativene ((±)- and (+)-2, resp.) were synthesized efficiently by a sequence of nine and ten steps, respectively. The key sequence 10 [RIGHTWARDS ARROW] 16 [RIGHTWARDS ARROW] 3 is the first strategic application of an intramolecular photoaddition/retro-aldolization ...