Srikrishna, A and Gharpure, SJ (2002) Chiral synthons from carvone, Part 56. Enantiospecific synthesis of (-)-4-thiocyanatoneopupukeanane. In: ARKIVOC (part 7). pp. 52-62.
Full text not available from this repository. (Request a copy)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 |
|---|---|
| Publication: | ARKIVOC |
| Publisher: | ARKAT FOUNDATION |
| Additional Information: | Copyright of this article belongs to ARKAT FOUNDATION. |
| Department/Centre: | Division of Chemical Sciences > Organic Chemistry |
| Date Deposited: | 22 Jul 2011 09:43 |
| Last Modified: | 23 Oct 2018 07:53 |
| URI: | http://eprints.iisc.ac.in/id/eprint/39048 |
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