Tetrahedron

[6+ 3] Cycloaddition of pentafulvenes with 3-oxidopyrylium betaine: a novel methodology toward the synthesis of 5–8 fused oxabridged cyclooctanoids

…, MM Bhadbhade, GV Bhosekar, KV Radhakrishnan

Index: Krishnan, K. Syam; Sajisha; Anas; Suresh; Bhadbhade, Mohan M.; Bhosekar, Gaurav V.; Radhakrishnan Tetrahedron, 2006 , vol. 62, # 25 p. 5952 - 5961

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Citation Number: 22

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, ...