An Improved Synthetic Route to Angularly Functionalized Hydrofluorene Derivatives through Pd(0)-Catalyzed Heck Reaction

Mainak Banerjee; Ranjan Mukhopadhyay; Basudeb Achari; Asish K. Banerjee

doi:10.1055/s-2006-926408

PAPER

An Improved Synthetic Route to Angularly Functionalized Hydrofluorene Derivatives through Pd(0)-Catalyzed Heck Reaction

Mainak Banerjee, Ranjan Mukhopadhyay, Basudeb Achari, Asish K. Banerjee*
Medicinal Chemistry Division, Indian Institute of Chemical Biology, 4 Raja S. C. Mullick Road, Kolkata 700032, India
Fax: +91(33)24735197; e-Mail: ashisbanerjee@iicb.res.in;

Abstract

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Abstract

4a-Substituted 1,1-dimethyl or 1-carbomethoxy-1-methyl hydrofluorenes carrying various substituents in the aromatic ring could be conveniently synthesized by Pd(0)-catalyzed Heck reaction. The required bromobenzyl-substituted ethylidene cyclohexane substrates were derived from Hagemann’s ester (methyl analogue) via condensation with appropriate benzyl bromide, hydrolytic decarboxylation of the ester, 1,4-addition of methyl or cyano group followed by necessary functional group manipulation, and Wittig olefination. Simple organic transformations converted the vinyl group to carboxy, formyl or hydroxymethyl. The ring juncture stereochemistry of the products could be ascertained by correlation approach.

Key words

4a-substituted hydrofluorenes - Heck reaction - Wittig reaction - Hagemann’s ester

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