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Enantioselective Total Synthesis of Fluvirucinin B1

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posted on 04.04.2016, 19:37 by Guillaume Guignard, Núria Llor, Elies Molins, Joan Bosch, Mercedes Amat
A convergent synthesis of fluvirucinin B1 from acid ent-6a and nitrile ent-9, involving an organocopper coupling, a stereoselective allylation, a ring-closing metathesis reaction, and a stereoselective hydrogenation as the key steps, is reported. The starting building blocks have been prepared in a straightforward manner from a common phenylglycinol-derived lactam 1. An unprecedented regioselective oxidation of phenylglycinol-derived secondary amines 5 to carboxylic acids 6 has been developed.