Chiral synthons from carvone. Part 4. Radical cyclization strategies to bridged systems. Synthesis of bicyclo[3.2.1]octan-3-ones from (S)-carvone

Srikrishna, A and Hemamalini, P (1990) Chiral synthons from carvone. Part 4. Radical cyclization strategies to bridged systems. Synthesis of bicyclo[3.2.1]octan-3-ones from (S)-carvone. In: Journal of Organic Chemistry, 55 (16). pp. 4883-4887.

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Abstract

Radical cyclization of the bromo enones 2a-e, obtained by regiospecific bromoetherification reaction on theelectron-rich double bond of (S)-carvone (l), furnished regio- and stereospecifically bicyclo[3.2.1]octan-3-ones 3a-e and 4a-e. Analogously, radical cyclizations of the alcohols 6 and 7 gave bicyclo[3.2.1]octan-3-ols 8 and 9,and the bromo enones lla,b gave the bridgehead-substituted bicyclo[3.2.l]octan-3-ones 12a,b and 13a,b.

Item Type:	Journal Article
Publication:	Journal of Organic Chemistry
Publisher:	American Chemical Society
Additional Information:	copyright of this article belongs to American Chemical Society
Department/Centre:	Division of Chemical Sciences > Organic Chemistry
Date Deposited:	08 Feb 2008
Last Modified:	19 Sep 2010 04:41
URI:	http://eprints.iisc.ac.in/id/eprint/12706

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