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An enantiodivergent protocol from R-(-)-carvone: synthesis of dihydroagarofuran sesquiterpenoid 1-deacetoxy-ent-orbiculin A

Kumaran, Senthil R and Mehta, Goverdhan (2015) An enantiodivergent protocol from R-(-)-carvone: synthesis of dihydroagarofuran sesquiterpenoid 1-deacetoxy-ent-orbiculin A. In: TETRAHEDRON, 71 (10). pp. 1547-1554.

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Official URL: http://dx.doi.org/10.1016/j.tet.2015.01.033

Abstract

A strategy for achieving enantiodivergency from R-(-)-carvone in the context of synthesis of eudesmanes and dihydroagarofurans is disclosed, which involves, among other things, sequential setting of the C10 quaternary centre and recreation of the desired C7 isopropyl stereochemistry to enter the antipodal series. A synthesis of 1-deacetoxy-ent-orbiculin has been achieved as a demonstration of the effectiveness and applicability of this approach. (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; Enantiodivergent synthesis; Dihydroagarofurans; Ring closure metathesis; Rubottom oxidation
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Depositing User: Id for Latest eprints
Date Deposited: 24 Apr 2015 05:38
Last Modified: 24 Apr 2015 05:38
URI: http://eprints.iisc.ac.in/id/eprint/51372

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