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Enantiospecific total synthesis (-)-4-hiocyanatoneopupukeanane

Srikrishna, A and Gharpure, Santosh J (2001) Enantiospecific total synthesis (-)-4-hiocyanatoneopupukeanane. In: Journal Of Organic Chemistry, 66 (12). pp. 4105-4462.

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Official URL: http://pubs.acs.org/doi/pdf/10.1021/jo0102765

Abstract

Enantiospecific synthesis of the natural enantiomer of the marine sesquiterpene (-)-4-thiocyanatoneopupukeanane (6) is described. The bicyclo[2.2.2]octanecarboxylate 14, obtained from (R)- carvone via Michael-Michael reaction, was transformed into neopupukeananedione 12 by employing rhodium acetate catalyzed intramolecular C-H insertion of the diazo ketones 16 or 19 as the key reaction. Regioselective deoxygenation of the C-2 ketone transformed the dione 12 into neopupukean-4-one 10. Alternately, the keto ester 18 was also transformed into neopupukean-4-one 10 via regioselective deoxygenation of the ketone in 18 followed by intramolecular rhodium carbenoid C-H insertion of the diazo ketone 31. Finally, neopupukean-4-one 10 was transformed into (-)-4-thiocyanatoneopupukeanane 6 via the alcohol 32 and the mesylate 33.

Item Type: Journal Article
Additional Information: Copyright of this article belongs to American Chemical Society.
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Date Deposited: 03 Jun 2009 06:21
Last Modified: 19 Sep 2010 04:54
URI: http://eprints.iisc.ernet.in/id/eprint/16892

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