Construction of the 3-prenyl-4-oxa-tricyclo$[4.3.1.0^{3,7}]$-dec-8-en-2-one core of caged xanthonoid natural products via tandem Wessely oxidation–intramolecular [4+2] cycloaddition

Mehta, Goverdhan and Maity, Pulakesh (2008) Construction of the 3-prenyl-4-oxa-tricyclo$[4.3.1.0^{3,7}]$-dec-8-en-2-one core of caged xanthonoid natural products via tandem Wessely oxidation–intramolecular [4+2] cycloaddition. In: Tetrahedron Letters, 49 (2). pp. 318-322.

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Abstract

A two-step protocol based on tandem Wessely oxidation/intramolecular Diels–Alder reaction to provide general access to the 3-prenyl-4-oxa-tricyclo$[4.3.1.0^{3,7}]$dec-8-en-2-one core present in the caged Garcinia xanthonoids is demonstrated. These readily accessible tricyclic scaffolds also provide ready entry into a variety of substituted γ-lactones through a photochemical 1,3-acyl shift and decarbonylation.

Item Type:	Journal Article
Publication:	Tetrahedron Letters
Publisher:	Elsevier
Additional Information:	Copyright of this article belongs to Elsevier.
Department/Centre:	Division of Chemical Sciences > Organic Chemistry
Date Deposited:	08 Mar 2008
Last Modified:	19 Sep 2010 04:43
URI:	http://eprints.iisc.ac.in/id/eprint/13348

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