The Journal of Organic Chemistry

Synthetic studies on the ingenane diterpenes. Construction of a tetracyclic 8-isoingenane model

JH Rigby, SV Cuisiat

Index: Rigby, James H.; Cuisiat, Stephane V. Journal of Organic Chemistry, 1993 , vol. 58, # 23 p. 6286 - 6291

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Citation Number: 29

Abstract

A thermally allowed tropone-diene [6u+ 47rI cycloaddition is employed to produce a functionally rich BC ring building block for the construction of 8-isoingenol intermediates. Bridgehead enolate alkylation followed by aldol condensation is used to install the elements of the A-ring. Stereo-and regioselective bis-hydroxylation at C-13 and-14 of the C-ring followed by activation as the correaponding bis-mesyloxy derivative and treatment with ...