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Issue 12, 1988
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Studies on a new route to (±)-copaene and (±)-ylangene


Elaboration of the perhydroazulene ring system formed by the intramolecular cycloaddition of a dienyl-substituted 3-oxidopyrylium has generated key intermediates used in the total synthesis of the α- and β-series of the copaene and ylangene sesquiterpene hydrocarbons. During the synthesis of the β-series of compounds selective protection of an olefinic bond was achieved by thiol addition; protection in this manner preventing migration of the double bond from an exocyclic to endocyclic position during the perhydroazulene to decalone rearrangement.

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Article information

J. Chem. Soc., Perkin Trans. 1, 1988, 3223-3228
Article type

Studies on a new route to (±)-copaene and (±)-ylangene

D. A. Archer, S. M. Bromidge and P. G. Sammes, J. Chem. Soc., Perkin Trans. 1, 1988, 3223
DOI: 10.1039/P19880003223

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