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

Srikrishna, Adusumilli and Vijaykumar, Dange (2000) An enantiospecific approach to pinguisanes from (R)-carvone. Total synthesis of (+)-pinguisenol. In: Perkin 1 (16). pp. 2583-2589.

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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.

Item Type: Journal Article
Publication: Perkin 1
Publisher: Royal Society of Chemistry
Additional Information: Copyright of this article belongs to Royal Society of Chemistry.
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Date Deposited: 23 Aug 2010 07:39
Last Modified: 19 Sep 2010 06:14
URI: http://eprints.iisc.ac.in/id/eprint/31446

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