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An Enantiospecific Approach to Tricyclic Sesquiterpenes Mayurone and Thujopsenes

Srikrishna, A and Anebouselvy, K (2001) An Enantiospecific Approach to Tricyclic Sesquiterpenes Mayurone and Thujopsenes. In: Journal of Organic Chemistry, 66 (21). pp. 7102-7106.

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An enantiospecific approach to mayurone and thujopsenes, sesquiterpenes containing three contiguous quaternary carbon atoms, starting from (R)-carvone (8), is described.(S)-3,4,4-Trimethylcarvone (7), obtained from (R)-carvone, was transformed into the bicyclo[2.2.2]octanone 13 via regioselective intramolecular alkylation of the allyl bromide 11. Regioselective ozonolysis and Criegee fragmentation of the bicyclic ketone 13 furnished the keto ester 14. Reductive deoxygenation followed by one-carbon homologation transformed the keto ester 19 into the ester 6. Intramolecular cyclopropanation of the diazo ketone 25, derived from the acid 5, furnished (-)-dihydromayurone (4), thus constituting a formal enantiospecific synthesis of mayurone and thujopsenes.

Item Type: Journal Article
Publication: Journal of Organic Chemistry
Publisher: American Chemical Society
Additional Information: Copyright of this article belongs to American Chemical Society.
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Date Deposited: 24 Sep 2008 09:09
Last Modified: 19 Sep 2010 04:49
URI: http://eprints.iisc.ac.in/id/eprint/15881

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