Enantiospecific synthesis of (−)-4-thiocyanatoneopupukeanane

Srikrishna, A. ; Gharpure, Santosh J. (2002) Enantiospecific synthesis of (−)-4-thiocyanatoneopupukeanane ARKIVOC: Online Journal of Organic Chemistry, 2002 . pp. 52-62. ISSN 1551-7004

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Official URL: http://www.arkat-usa.org/get-file/20354/


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:Article
Source:Copyright of this article belongs to Arkat-USA, Inc.
Keywords:Carvone; Marine Sesquiterpenes; Michael-michael Reaction; Intramolecular Cyclopropanation Reaction; Regioselective Cyclopropane Ring Cleavage
ID Code:51577
Deposited On:28 Jul 2011 14:31
Last Modified:28 Jul 2011 14:31

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