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Synthetic studies towards the novel fomannosane sesquiterpenoid illudosin: framework construction

Mehta, Goverdhan and Sreenivas, K (2003) Synthetic studies towards the novel fomannosane sesquiterpenoid illudosin: framework construction. In: Tetrahedron, 59 (19). pp. 3475-3480.

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Abstract

A synthetic approach to the novel fomannosane sesquiterpene natural product illudosin benzene 2 from the diquinane precursor benzene 5, readily available in turn from commercial 1,5- cyclooctadiene, is delineated. The key steps are the stereoselective construction of the cis, anti, cistricyclo$[6.2.0.0^2^,^6]$ decane system, strategic C-C bond disengagement through Baeyer–Villiger oxidation and functional group adjustments to deliver the carbocyclic core benzene 18 present in the natural product.

Item Type: Journal Article
Additional Information: Copyright for this article belongs to Elsevier Science.
Keywords: Baeyer–Villiger oxidation;farnesyl pyrophosphate;cyclobutanoids;photocycloaddition;enone transposition
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Date Deposited: 25 Jan 2005
Last Modified: 19 Sep 2010 04:17
URI: http://eprints.iisc.ernet.in/id/eprint/2665

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