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Issue 16, 2000
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An enantiospecific approach to pinguisanes from (R)-carvone. Total synthesis of (+)-pinguisenol

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Abstract

Enantiospecific total synthesis of (+)-pinguisenol 1, a sesquiterpene containing a cis-1,2,6,7-tetramethylbicyclo[4.3.0]nonane carbon framework incorporating two vicinal quaternary carbon atoms and four cis-oriented methyl groups on four contiguous carbon atoms, isolated from a liverwort, is described. The orthoester Claisen rearrangement of the allyl alcohol 9, obtained from (R)-carvone, generates the ester 12. Intramolecular cyclopropanation of the diazo ketone 13, derived from the ester 12, furnishes the tricyclic ketone 7. Degradation of the isopropenyl group followed by regioselective reductive cyclopropane ring cleavage transforms compound 7 into the hydroxy ketone 21. Wolff–Kishner reduction of the hydroxy ketone 21 followed by oxidation and Grignard reaction furnishes pinguisenol (+)-1.

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Publication details

The article was received on 14 Jun 2000, accepted on 04 Jul 2000 and first published on 01 Aug 2000


Article type: Paper
DOI: 10.1039/B004770H
J. Chem. Soc., Perkin Trans. 1, 2000, 2583-2589

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    An enantiospecific approach to pinguisanes from (R)-carvone. Total synthesis of (+)-pinguisenol

    A. Srikrishna and D. Vijaykumar, J. Chem. Soc., Perkin Trans. 1, 2000, 2583
    DOI: 10.1039/B004770H

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