Please use this identifier to cite or link to this item: http://localhost:8080/xmlui/handle/123456789/2195
Title: [6+3] cycloaddition of pentafulvenes with 3-oxidopyrylium betaine: a novel methodology toward the synthesis of 5-8 fused oxabridged cyclooctanoids
Authors: Syam Krishnan, K
Sajisha, V S
Anas, S
Suresh, C H
Bhadbhade, M M
Bhosekar, G V
Radhakrishnan, K V
Keywords: Fulvenes
Oxidopyrylium betaine
[6+3] cycloaddition
Oxabridged cyclooctanoids
Catalyzed 4+2+2 cycloaddition
8-membered rings
Schisandra lancifolia
Facile synthesis
Crystal structure
Alkenes
Issue Date: 2006
Publisher: Elsevier
Citation: Tetrahedron 62(25):5952-5961;19 Jun 2006
Abstract: Pentafulvenes undergo a facile [6+3] cycloaddition with 3-oxidopyrylium betaine, generated from the corresponding pyranulose acetate, leading to the formation of 5-8 fused oxabridged cyclooctanoids. The product is formed by a [6+3] cycloaddition, followed by a 1,5-hydrogen shift of the initially formed [6+3] adduct. The reaction was found to be general and a number of fulvenes with a wide range of substituents at the exocyclic double bond, that is, at the C6 position followed a similar reactivity pattern. The [6+3] adduct, a 5-8 fused oxabridged cyclooctanoid, is potentially amenable to a number of synthetic transformations due to the presence of an alpha, beta-unsaturated ketone and cyclopentadiene part. By selecting appropriately substituted fulvene and pyranulose acetates, it is possible to use this methodology for the synthesis of a wide range of 5-8 fused cyclooctanoids. The experimental results have been rationalized on the basis of theoretical calculations.
URI: http://ir.niist.res.in:8080/jspui/handle/123456789/2195
ISSN: 0040-4020
Appears in Collections:2006

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