A stereoselective total synthesis of (+)-$\alpha$-herbertenol

Srikrishna, A and Babu, Chandrasekhar N and Rao, Srinivasa M (2004) A stereoselective total synthesis of (+)-$\alpha$-herbertenol. In: Tetrahedron, 60 (9). pp. 2125-2130.

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Abstract

A stereoselective total synthesis of (+)-$\alpha$-herbertenol starting from the allyl alcohol 12, readily available in three steps from the monoterpene (R)-limonene, is described. Claisen rearrangement of the aryl allyl ether 10 and concomitant cyclisation furnished a 5:3 mixture of the tricyclic compounds 13 and 14. Degradation of the isopropenyl group followed by cleavage of the central ring and functional group manipulation transformed 13 into (+)-$\alpha$-herbertenol (1b).

Item Type:	Journal Article
Publication:	Tetrahedron
Publisher:	Elsevier
Additional Information:	The copyright belongs to Elsevier.
Keywords:	Herbertenediol;Mastigophorenes;Cyclopentane
Department/Centre:	Division of Chemical Sciences > Organic Chemistry
Date Deposited:	29 May 2006
Last Modified:	19 Sep 2010 04:27
URI:	http://eprints.iisc.ac.in/id/eprint/7083

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