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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