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Molecules 2014, 19(1), 1238-1249; doi:10.3390/molecules19011238
Article

Construction of the 1,2-Dialkenylcyclohexane Framework via Ireland-Claisen Rearrangement and Intramolecular Barbier Reaction: Application to the Synthesis of (±)-Geijerone and a Diastereoisomeric Mixture with Its 5-Epimer

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Key Laboratory of Structure-Based Drug Design and Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang 110016, Liaoning, China
* Author to whom correspondence should be addressed.
Received: 17 December 2013 / Revised: 14 January 2014 / Accepted: 15 January 2014 / Published: 20 January 2014
(This article belongs to the Section Organic Synthesis)
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Abstract

The elemene-type terpenoids, which possess various biological activities, contain a syn- or anti-1,2-dialkenylcyclohexane framework. An efficient synthetic route to the syn- and anti-1,2-dialkenylcyclohexane core and its application in the synthesis of (±)-geijerone and its diastereomer is reported. Construction of the syn- and anti-1,2-dialkenyl moiety was achieved via Ireland-Claisen rearrangement of the (E)-allylic ester, and the cyclohexanone moiety was derived from the iodoaldehyde via intramolecular Barbier reaction. The synthetic strategy allows rapid access to various epimers and analogues of elemene-type products.
Keywords: 1,2-dialkenylcyclohexane; (±)-geijerone; Ireland-Claisen rearrangement; intramolecular barbier reaction; synthesis 1,2-dialkenylcyclohexane; (±)-geijerone; Ireland-Claisen rearrangement; intramolecular barbier reaction; synthesis
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).
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Liang, D.; Gao, N.; Liu, W.; Dong, J. Construction of the 1,2-Dialkenylcyclohexane Framework via Ireland-Claisen Rearrangement and Intramolecular Barbier Reaction: Application to the Synthesis of (±)-Geijerone and a Diastereoisomeric Mixture with Its 5-Epimer. Molecules 2014, 19, 1238-1249.

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