Synthetic studies involving bridgehead alpha,beta-unsaturated ketones: Protocols for regiocontrolled alpha-methylation

[摘要]：Bicyclo[5.3.1]undec-10-en-9-one (3) has been converted via two routes into the 10-methyl homolog 11. The first pathway consists of alpha-phenylthiomethylation and subsequent desulfurization with Raney nickel. The second sequence proceeds via the 1,2-addition of ethylmagnesium bromide followed by dihydroxylation, ring cleavage with lead tetraacetate, and base-promoted cyclization.

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