Srikrishna, A and Gharpure, SJ (2002) Chiral synthons from carvone, Part 56. Enantiospecific synthesis of (-)-4-thiocyanatoneopupukeanane. In: ARKIVOC (part 7). 52-62 .Full text not available from this repository.
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.|
|Date Deposited:||22 Jul 2011 09:43|
|Last Modified:||22 Jul 2011 09:43|
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