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ChemInform Abstract: Synthesis Based on Cyclohexadienes. Part 16. Synthesis of Methyl 2,7-Dimethyltricyclo (5.2.2.01,5)undec-5-ene-6-carboxylates

Shanker, PS and Rao, GSRS (1995) ChemInform Abstract: Synthesis Based on Cyclohexadienes. Part 16. Synthesis of Methyl 2,7-Dimethyltricyclo (5.2.2.01,5)undec-5-ene-6-carboxylates. In: Indian Journal of Chemistry - Section B: Organic and Medicinal Chemistry, 34 (4). pp. 271-279.

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Official URL: http://onlinelibrary.wiley.com/doi/10.1002/chin.19...

Abstract

Synthesis of methyl 2, 7-dimethyltricyclo{5.2.2.0(1,5}undec-5-en-6-carboxylates, the tricyclic skeleton present in (+)-allo-cedrol (1) is described using the Diels-Alder strategy. Thus, Birch reduction of the aromatic acid 8 gives 5, the methyl ester of which is isomerised with DBU to a 1:1 mixture of the dienes 6 and 4. Cycloaddition of this mixture with 2-chloroacrylonitrile followed by hydrolysis yields the ketone 60 having the tricyclo{5.2.2.0(1.5)}undec-5-ene framework. Similar reaction with methyl vinyl ketone affords the regioisomeric adducts 61 and 62.

Item Type: Journal Article
Additional Information: Copyright of this article belongs to National Institute of Science Communication and Information Resources.
Keywords: terpenes
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Date Deposited: 26 May 2011 07:23
Last Modified: 26 May 2011 07:23
URI: http://eprints.iisc.ernet.in/id/eprint/37946

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