Synthetic study of TAUTOMYCIN (cas 109946-35-2). Part 2: Synthesis of Ichihara's fragment based on regioselective enzymatic acetylation of complex molecule

Add time:08/03/2019    Source:sciencedirect.com

Formal synthesis of tautomycin, which inhibits type 1 and type 2A protein phosphatases, was achieved. Spiroketal diol 21 was synthesized from alcohol 2 or 11. The regioselective enzymatic acetylation of 21 with the lipase ‘Amano PS’ gave monoacetate 23 in 90% yield, which was converted into Ichihara's intermediate 31 based on Julia coupling and Wittig homologation.

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