We are reporting the diastereoselective synthesis of advanced fragments of zincophorin, namely its C1�C13 subunit, as well as isomers thereof. This is achieved using a two-reaction sequence: a Mukaiyama aldolization using a tetrasubstituted enoxysilane and a hydrogen-transfer reaction, both under Lewis acid control. Selection of the optimal synthetic route to construct the polypropionate sequence was found to be influenced by the number of complexation sites that can interfere in the aldol step under bidentate Lewis acid control.

Diastereoselective synthesis of advanced fragments of zincophorin and related isomers via a combined approach of Mukaiyama aldol reaction and radical reduction

243rd National Meeting (2012)

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