ChemInform Abstract: Chiral Synthons from Carvone. Part 44. An Enantiospecific Approach to Pinguisanes from (R)-Carvone. Total Synthesis of (+)-Pinguisenol.
Abstract
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ChemInform Abstract
The title compound is prepared by an enantiospecific approach starting from (R)-carvone (I) by employing a Claisen rearrangement, an intramolecular diazo ketone cyclopropanation, a degradation of the isopropenyl group, and a regioselective reductive cyclopropane ring-cleavage sequence. Hydroxy ketone (XII) is finally transformed by Wolff—Kishner reduction, oxidation, and Grignard reaction to furnish the target sesquiterpene.
