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A versatile, RCM based approach to eudesmane and dihydroagarofuran sesquiterpenoids from (-)-carvone: a formal synthesis of (-)-isocelorbicol

Kumaran, Senthil R and Mehta, Goverdhan (2015) A versatile, RCM based approach to eudesmane and dihydroagarofuran sesquiterpenoids from (-)-carvone: a formal synthesis of (-)-isocelorbicol. In: TETRAHEDRON, 71 (11). pp. 1718-1731.

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Official URL: http://dx.doi.org/10.1016/j.tet.2015.01.039

Abstract

An enantiospecific and diversity oriented approach to a range of functionalized eudesmane, nor-, iso-, and dihydroagarofuran frameworks from (-)-carvone is delineated. The cornerstone of this approach is the installation of the quaternary carbon center through reductive opening of the carvone epoxide and setting-up of RCM reaction to generate the bicyclic eudesmane framework. Various options like carbocation mediated oxycyclization and intramolecular hydroxy directed epoxide opening have been explored for the construction of the bridged tetrahydrofuran moiety. Among the several eudesmane and dihydroagarofurans accessed during the present study, one has been previously elaborated to iso-celorbicol, thus constituting its formal synthesis. (C) 2015 Elsevier Ltd. All rights reserved.

Item Type: Journal Article
Additional Information: Copy right for this article belongs to the PERGAMON-ELSEVIER SCIENCE LTD, THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND
Keywords: Sesquiterpenoids; Ring closure metathesis; Oxycyclization; Epoxidation; Natural products synthesis
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Depositing User: Id for Latest eprints
Date Deposited: 20 Apr 2015 10:59
Last Modified: 20 Apr 2015 10:59
URI: http://eprints.iisc.ac.in/id/eprint/51281

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