Srikrishna, A and Reddy, Jagadeeswar T (2001) Chiral synthons from carvone. Part 50.Enantiospecific approaches to both enantiomers of bicyclo[4.3.0]nonane-,8-dione derivatives. In: Journal of The Chemical Society-Perkin Transactions 1 (1). pp. 2040-2046.
Chiral_synthons_from_carvone.pdf - Published Version
Restricted to Registered users only
Download (159Kb) | Request a copy
Enantiospecific synthesis of both enantiomeric forms of bicyclo[4.3.0]nonane-3,8-dione derivatives has been described starting from (R)-carvone employing two different cyclopentannulation methodologies. Thus, in the first methodology, carveol (5) was converted into tricyclic ketone 4 employing a Claisen rearrangement and intramolecular diazo ketone cyclopropanation reactions. Degradation of the isopropenyl group followed by cyclopropane cleavage and cuprate addition generated the dione (-)-12a. Whereas, a Wacker mediated cyclopentannulation of (R)-carvone via the dione 15 furnished the enone 17. Functional group manipulation including the degradation of isopropenyl group transformed the enone 17 into the dione (+)-12a, which on regioselective ketalisation generated the ketoketal (+)-2.
|Item Type:||Journal Article|
|Additional Information:||Copyright of this article belongs to The Royal Society of Chemistry|
|Department/Centre:||Division of Chemical Sciences > Organic Chemistry|
|Date Deposited:||19 Dec 2008 14:30|
|Last Modified:||01 Jul 2011 07:57|
Actions (login required)