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Radical cyclization strategies to terpenoids; syntheses of (±)-β-cuparenone, (±)-laurene and epilaurenes

Srikrishna, A and Sundarababu, G (1991) Radical cyclization strategies to terpenoids; syntheses of (±)-β-cuparenone, (±)-laurene and epilaurenes. In: Tetrahedron, 47 (3). pp. 481-496.

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Official URL: http://dx.doi.org/10.1016/S0040-4020(01)90504-6

Abstract

Radical cyclization of the bromide Image , obtained in 5 steps from the ketone Image , furnished exclusively Image Image 6-endo trig cyclization with out any observable amount of 5-exo trig product Image . 5-Exo dig radical cyclizatlon of the bromo acetate Image , prepared from Image Image the aldehyde Image , followed by routine transformations furnished the cyclopentenone Image , an immediate precursor to β-cuparenone (Image ). Similarly, total synthesis of laurenes Image and Image was achieved Image the 5-exo dig radical cyclization of the xanthate Image , obtained from the aldehyde Image .Syntheses to title compounds based on 5-exo-dig radical cyclisation, along with two unsuccessful approaches to cuparene, are described.

Item Type: Journal Article
Additional Information: Copyright of this article belongs to Elsevier science.
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Date Deposited: 30 Nov 2010 06:47
Last Modified: 30 Nov 2010 06:47
URI: http://eprints.iisc.ernet.in/id/eprint/34063

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