A new synthesis of tricyclic sesquiterpene (±)-sterpurene

Mehta, Goverdhan and Sreenivas, K (2002) A new synthesis of tricyclic sesquiterpene (±)-sterpurene. In: Tetrahedron Letters, 43 (4). pp. 703-706.

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Abstract

A new synthesis of tricyclic sesquiterpene, sterpurene 1 is reported. An intermolecular [2+2]-photocycloaddition 14→ 15 serves as a key step, which is promoted through the stabilisation of the enone excited state through a beta-carbomethoxy substituent on the alpha,beta-unsaturated enone moiety. A tricyclo[6.3.0.03,6]undecane based advanced intermediate 19 en route to 1, has been fragmented to the bicyclo[6.3.0]undecane system 27 present in the asteriscane-type sesquiterpenoids.

Item Type:	Journal Article
Publication:	Tetrahedron Letters
Publisher:	Elsevier Science
Additional Information:	Copyright for this article belongs to Elsevier Science.
Department/Centre:	Division of Chemical Sciences > Organic Chemistry
Date Deposited:	03 Aug 2004
Last Modified:	19 Sep 2010 04:14
URI:	http://eprints.iisc.ac.in/id/eprint/1228

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