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Enantiospecific synthesis of thaps-8-en-5-ol via stereospecific intramolecular chirality transfer

Srikrishna, A and Anebouselvy, K (2008) Enantiospecific synthesis of thaps-8-en-5-ol via stereospecific intramolecular chirality transfer. In: Indian Journal of Chemistry - Section B: Organic and Medicinal Chemistry, 47 (3). pp. 449-459.

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Abstract

Enantiospecific synthesis of thaps-8-en-5-ol, comprising of the carbon framework of a small group of sesquiterpenes containing three contiguous quaternary carbon atoms has been described. (R)-Carvone has been employed as the chiral starting material and a combination of intramolecular alkyation and Criegec fragmentation have been employed for intramolecular stereospecific transfer of the chirality. An intramolecular diazoketone cyclopropanation and regioselective cyclopropane ring cleavage reactions have been employed for the creation of the three requisite contiguous quaternary carbon atoms.

Item Type: Journal Article
Additional Information: Copyright of this article belongs to National Institute of Science Communication and Information Resources.
Keywords: enantiospecific synthesis;thaps-8-en-5-ol;sesquiterpenes;(R)-Carvone;Criegee fragmentation.
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Date Deposited: 30 Mar 2010 11:42
Last Modified: 30 Mar 2010 11:42
URI: http://eprints.iisc.ernet.in/id/eprint/26286

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