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

✍ Scribed by A. Srikrishna; T. Jagadeeswar Reddy

Publisher: Elsevier Science
Year: 1998
Tongue: French
Weight: 525 KB
Volume: 54
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(98)00672-3

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✦ Synopsis

Synthesis of the chiral bicyclic ketone mentioned in the title starting from Rcarvone, 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 Waeker 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 eyclisation based strategy transformed the bicyclic ketone 3 into chiral 7-epibakkenolide-A.

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