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/
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: | 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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