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Enantiospecific synthesis of (+)-(1S,2R,6S)-1,2-dimethylbicyclo[4.3.0]nonan-8-one and (-)-7-epibakkenolide-A

Srikrishna, A and Reddy, Jagadeeswar T (1998) Enantiospecific synthesis of (+)-(1S,2R,6S)-1,2-dimethylbicyclo[4.3.0]nonan-8-one and (-)-7-epibakkenolide-A. In: Tetrahedron, 54 (38). pp. 11517-11524.

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Synthesis of the chiral bicyclic ketone mentioned in the title starting from R-carvone, and its elaboration to 7-epibakkenolide-A is described. Conjugate addition of dimethyl copperlithium to R-carvone followed by alkylation of the intermediate enolate generated the allylated compound 6, which was transformed into the diketone 12 via a sequence of reactions comprising regiospecific Wacker oxidation, ozonation-Criegee rearrangement as key reactions. Intramolecular aldol condensation followed by catalytic hydrogenation converted the diketone 12 into the bicyclic ketone (+)-3, the optical antipode of the compound derived from the sesquiterpenes bakkenolide-A and fukinone. A 5-exo-dig radical cyclisation based strategy transformed the bicyclic ketone 3 into chiral 7-epibakkenolide-A.

Item Type: Journal Article
Publication: Tetrahedron
Publisher: Elsevier Science
Additional Information: Copyright of this article belongs to Elsevier Science.
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Date Deposited: 03 Jun 2009 06:14
Last Modified: 03 Jun 2009 06:14
URI: http://eprints.iisc.ac.in/id/eprint/18562

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