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Chiral synthons from carvone. Part 50.Enantiospecific approaches to both enantiomers of bicyclo[4.3.0]nonane-,8-dione derivatives

Srikrishna, A and Reddy, Jagadeeswar T (2001) Chiral synthons from carvone. Part 50.Enantiospecific approaches to both enantiomers of bicyclo[4.3.0]nonane-,8-dione derivatives. In: Journal of The Chemical Society-Perkin Transactions 1 (1). pp. 2040-2046.

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Abstract

Enantiospecific synthesis of both enantiomeric forms of bicyclo[4.3.0]nonane-3,8-dione derivatives has been described starting from (R)-carvone employing two different cyclopentannulation methodologies. Thus, in the first methodology, carveol (5) was converted into tricyclic ketone 4 employing a Claisen rearrangement and intramolecular diazo ketone cyclopropanation reactions. Degradation of the isopropenyl group followed by cyclopropane cleavage and cuprate addition generated the dione (-)-12a. Whereas, a Wacker mediated cyclopentannulation of (R)-carvone via the dione 15 furnished the enone 17. Functional group manipulation including the degradation of isopropenyl group transformed the enone 17 into the dione (+)-12a, which on regioselective ketalisation generated the ketoketal (+)-2.

Item Type: Journal Article
Additional Information: Copyright of this article belongs to The Royal Society of Chemistry
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Date Deposited: 19 Dec 2008 14:30
Last Modified: 01 Jul 2011 07:57
URI: http://eprints.iisc.ernet.in/id/eprint/16643

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