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Radical Cyclization Strategies to Bridged Systems. Synthesis of Bicyclo[3.2.1]octan-3-ones from (S)-Carvone

Srikrishna, A and Hemamalini, P (1990) 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 I (R = H, R1R2 = O, R3 = Me, Et, H, Ac, CH2Ph), obtained by regiospecific bromoetherification at the electron-rich double bond of (S)-carvone, gave regio- and stereospecificially bicyclo[3.2.1]octan-3-ones II (R = H, R1R2 = O; R3 as above). Analogously, radical cyclizations of I (R = R1 = H, R2 = OH) gave II (R = R1 = H, R2 = OH) and I (R = Me, R1R2 = O) gave II (R = Me, R1R2 = O).

Item Type: Journal Article
Additional Information: Copyright of this article belongs to ACS publications
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Date Deposited: 20 Dec 2007
Last Modified: 19 Sep 2010 04:41
URI: http://eprints.iisc.ernet.in/id/eprint/12553

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