Enantioselective synthesis of natural combretastatin

Article abstract of DOI:10.1016/0957-4166(96)00115-2

In a process which appears to be general for the enantioselective synthesis of oxysubstituted 1,2-diarylethanols, a 4-methoxy-3-silyloxyphenyllithium, obtained by bromine-lithium exchange from the corresponding aryl bromide and t-butyllithium, added selectively at the b-carbon of (S)-2,3,4-trimethoxyphenyloxirane, elaborated from the corresponding styrene via Sharpless asymmetric dihydroxylation, to afford an adduct from which natural (-)-combretastatin was obtained by desilylation.