An enantiospecific approach to tricyclic sesquiterpenes mayurone and thujopsenes

Srikrishna, A. ; Anebouselvy, K. (2001) An enantiospecific approach to tricyclic sesquiterpenes mayurone and thujopsenes Journal of Organic Chemistry, 66 (21). pp. 7102-7106. ISSN 0022-3263

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Official URL: http://pubs.acs.org/doi/abs/10.1021/jo0105484

Related URL: http://dx.doi.org/10.1021/jo0105484

Abstract

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:Article
Source:Copyright of this article belongs to American Chemical Society.
ID Code:48729
Deposited On:15 Jul 2011 11:41
Last Modified:15 Jul 2011 11:41

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