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An Enantiospecific Approach to Tricyclic Sesquiterpenes Mayurone and Thujopsenes1
journal contribution
posted on 2001-09-20, 00:00 authored by A. Srikrishna, K. AnebouselvyAn 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.
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allyl bromide 11ester 6carvoneenantiospecific approachmayuronequaternary carbon atomsIntramolecular cyclopropanationRegioselective ozonolysisEnantiospecific Approachenantiospecific synthesisThujopsenes 1acid 5regioselective intramolecular alkylationTricyclic Sesquiterpenes Mayuroneketo ester 14Criegee fragmentationbicyclic ketone 13diazo ketone 25keto ester 19Reductive deoxygenationthujopsene
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