Synlett

Aromatics to Diquinanes: An Expeditious Synthesis of Tetramethylbicyclo [3.3. 0] octane Framework of Ptychanolide

V Singh, G Chandra, SM Mobin

Index: Singh, Vishwakarma; Chandra, Girish; Mobin, Shaikh M. Synlett, 2008 , # 20 p. 3111 - 3114

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Citation Number: 2

Abstract

Abstract An expeditious route to methyl-7-oxo-1, 4, 5, 8-tetramethylbicyclo [3.3. 0] octane-3- carboxylate from a simple aromatic precursor is described. Oxidative dearomatization of 2- hydroxymethyl-3, 4, 6-trimethylphenol into spiroepoxycyclohexa-2, 4-dienone, its cycloaddition and triplet-sensitized 1, 2-acyl shift, and stereochemical inversion are the key features of our methodology.

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