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

Srikrishna, Adusumilli ; Vijaykumar, Dange (2000) An enantiospecific approach to pinguisanes from (R)-carvone. Total synthesis of (+)-pinguisenol Journal of the Chemical Society, Perkin Transactions 1 (16). pp. 2583-2589. ISSN 0300-922X

Full text not available from this repository.

Official URL:

Related URL:


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:Article
Source:Copyright of this article belongs to Royal Society of Chemistry.
ID Code:48895
Deposited On:19 Jul 2011 08:44
Last Modified:19 Jul 2011 08:44

Repository Staff Only: item control page