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Enantioselective Synthesis of the Hydroazulene Core of 3α-Hydroxy-15-rippertene

✍ Scribed by Thomas Kreuzer; Peter Metz

Publisher
John Wiley and Sons
Year
2008
Tongue
English
Weight
270 KB
Volume
2008
Category
Article
ISSN
1434-193X

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✦ Synopsis

Abstract

As part of a project directed toward the total synthesis of the tetracyclic diterpene 3α‐hydroxy‐15‐rippertene, a constituent of the defense secretion of higher termites, a fast access to two advanced hydroazulene key intermediates has been achieved by starting from (–)‐isopulegol. A regio‐ and diastereoselective formal hydromethallylation and a regioselective ring expansion served as the key steps in the formation of the seven‐membered ring. Completion of the bicyclic title compounds was then achieved by cyclopentene annulation through diastereoselective conjugate addition of organocuprates and subsequent intramolecular aldol condensations.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

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