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Enantiospecific first total synthesis of (6S,7R)-silphiperfolan-6-ol

Srikrishna, A and Nagaraju, Gopalasetty and Sheth, Vishal M (2012) Enantiospecific first total synthesis of (6S,7R)-silphiperfolan-6-ol. In: Tetrahedron, 68 (12). pp. 2650-2656.

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Official URL: http://dx.doi.org/10.1016/j.tet.2012.01.063


Enantiospecific first total synthesis of the angular triquinane sesquiterpene (65,7R)-silphiperfolan-6-ol has been accomplished, starting from 2-(3-isopropenyl-2-methylene-1-methylcyclopent-1-yl)acetic acid (readily available from (R)-limonene) employing an efficient, regioselective intramolecular rhodium carbenoid insertion into the CH bond of a tertiary methyl group as the key step. (C) 2012 Elsevier Ltd. All rights reserved.

Item Type: Journal Article
Publication: Tetrahedron
Publisher: Elsevier Science
Additional Information: Copyright of this article belongs to Elsevier Science.
Keywords: Angular triquinanes;Silphiperfolane;Enantiospecific synthesis;Rhodium carbenoid CH insertion;Limonene
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Date Deposited: 01 May 2012 10:52
Last Modified: 01 May 2012 10:52
URI: http://eprints.iisc.ac.in/id/eprint/44343

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