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.
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