The stereoselective synthesis of the fully functionalized northern hemisphere of the marine natural product amphidinolide H2 is described. A vinylogous Mukaiyama aldol reaction and enzymatic desymmetrization of a meso compound are the key steps in the fragment synthesis. A stereoselective acetate aldol coupling and a 1,3-anti-reduction of the resulting b-hydroxy ketone complete the synthesis of the C14-C26 fragment.
The synthesis of the C19-C26 methyl ketone of amphidinolide H2 is described employing a stereoselective catalytic vinylogous Mukaiyama aldol reaction. Selective dihydroxylation and deoxygenation completes the synthesis of the C19-C26 segment.
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