73274-32-5Relevant articles and documents
Synthetic studies involving bridgehead a,/?-unsaturated ketones: protocols for regiocontrolled a-methylation
Paquette, Leo A.,Wang, Hui-Ling,Su, Zhuang
, p. 1123 - 1128 (1998)
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 a-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 basepromoted cyclization.