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Unprecedented formation of a 14-membered dihydropyran macrocycle via sequential olefin cross metathesis-intramolecular hetero Diels-Alder reaction

Prasad, Kavirayani R and Kumar, Mothish S (2013) Unprecedented formation of a 14-membered dihydropyran macrocycle via sequential olefin cross metathesis-intramolecular hetero Diels-Alder reaction. In: TETRAHEDRON, 69 (31). pp. 6512-6518.

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Official URL: http://dx.doi.org/10.1016/j.tet.2013.05.032

Abstract

Formation of a 2,3-dihydro-4H-pyran containing 14-membered macrocycle by sequential olefin cross metathesis and a highly regiospecific hetero Diels-Alder reaction was observed in the reaction of a hydroxydienone derived from tartaric acid with Grubbs' second generation catalyst. It was found that the free alcohol in the hydroxyenone led to the macrocycle formation, while protection of the hydroxy group formed the ring closing metathesis product. (C) 2013 Elsevier Ltd. All rights reserved.

Item Type: Journal Article
Additional Information: Copyright of this article is belongs to PERGAMON-ELSEVIER
Keywords: Macrolides; Olefin cross metathesis; Hetero Diels-Alder reaction; Tandem reactions
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Depositing User: Id for Latest eprints
Date Deposited: 20 Aug 2013 11:31
Last Modified: 20 Aug 2013 11:32
URI: http://eprints.iisc.ac.in/id/eprint/47028

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