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

Published inHelvetica chimica acta, vol. 67, no. 4, p. 1154-1167
Publication date1984-06-20
First online date2004-10-25
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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Citation (ISO format)
VON OPPOLZER, Wolfgang, GODEL, Thierry. Syntheses of (±)- and Enantiomerically Pure (+)-Longifolene and of (±)- and Enantiomerically Pure (+)-Sativene by an Intramolecular <i>de Mayo</i> Reaction. In: Helvetica chimica acta, 1984, vol. 67, n° 4, p. 1154–1167. doi: 10.1002/hlca.19840670429
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ISSN of the journal0018-019X
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