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

✍ Scribed by Wolfgang Oppolzer; Thierry Godel

Publisher
John Wiley and Sons
Year
1984
Tongue
German
Weight
973 KB
Volume
67
Category
Article
ISSN
0018-019X

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✦ Synopsis

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 → 16 → 3 is the first strategic application of an intramolecular photoaddition/retro‐aldolization sequence (intramolecular de Mayo reaction) in organic synthesis.

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