Enantioselective total syntheses of the novel tricyclic sesquiterpene hydrocarbons (+)- and (−)-kelsoene. Absolute configuration of the natural product

Mehta, Goverdhan and Srinivas, K (2001) Enantioselective total syntheses of the novel tricyclic sesquiterpene hydrocarbons (+)- and (−)-kelsoene. Absolute configuration of the natural product. In: Tetrahedron Letters, 42 (15). pp. 2855-2857.

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Abstract

Simple and preparatively efficacious lipase-catalysed kinetic resolution of endo,endo–cis-bicyclo[3.3.0]octane-2,6-diol rac-3 has provided ready access to bicyclo[3.3.0]octane-2,6-diones (−)-2 and (+)-2 of high enantiomeric purity. These C2-symmetric diones have been further elaborated to the sesquiterpene hydrocarbon (+)-kelsoene 1 and ent-kelsoene (−)-1, respectively, thereby establishing the absolute configuration of the natural product. In the light of these results, the absolute configuration assigned earlier to (+)-kelsoene needs to be revised as (+)-1.

Item Type:	Journal Article
Publication:	Tetrahedron Letters
Publisher:	Elsevier Science
Additional Information:	Copyright for this article belongs to Elsevier Science.
Department/Centre:	Division of Chemical Sciences > Organic Chemistry
Date Deposited:	01 Feb 2005
Last Modified:	19 Sep 2010 04:17
URI:	http://eprints.iisc.ac.in/id/eprint/2688

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