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Chiral synthons from carvone, Part 56. Enantiospecific synthesis of (-)-4-thiocyanatoneopupukeanane

Srikrishna, A and Gharpure, SJ (2002) Chiral synthons from carvone, Part 56. Enantiospecific synthesis of (-)-4-thiocyanatoneopupukeanane. In: ARKIVOC (part 7). 52-62 .

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Abstract

Enantiospecific total synthesis of the natural enantiomer of the marine sesquiterpene (-)-4-thiocyanatoneopupukeanane (6) is described. The bicyclo[2.2.2]octanonecarboxylate 11, obtained from (R)-carvone and methyl methacrylate via Michael-Michael reaction, was transformed into bicyclo[2.2.2]octenecarboxylic acid 8. Intramolecular cyclopropanation reaction of the diazo ketone 7, derived from the acid 8, followed by regioselective reductive cyclopropane ring cleavage generated neopupukeanol 20, which was transformed into (-)-4-thiocyanatoneopupukeanane 6.

Item Type: Journal Article
Additional Information: Copyright of this article belongs to ARKAT FOUNDATION.
Department/Centre: Others
Date Deposited: 22 Jul 2011 09:43
Last Modified: 22 Jul 2011 09:43
URI: http://eprints.iisc.ernet.in/id/eprint/39048

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