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Organocatalytic Michael addition, a convenient tool in total synthesis. First asymmetric synthesis of (-)-botryodiplodin

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Published in Tetrahedron Letters. 2003, vol. 44, no. 43, p. 7901-7904
Abstract The asymmetric Michael addition of propionaldehyde to (2E)-(3-nitro-but-2-enyloxymethyl)-benzene 8, catalyzed by the chiral diamine (S,S)-N-iPr-2,2'-bipyrrolidine, afforded, with 93% ee, a precursor 9 of (-)-botryodiplodin. The nitro functionality of 9 was converted to a ketone via a Nef reaction to give, after a few steps, the enantiomerically enriched (-)-botryodiplodin.
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ANDREY, Olivier, VIDONNE, Annick, ALEXAKIS, Alexandre. Organocatalytic Michael addition, a convenient tool in total synthesis. First asymmetric synthesis of (-)-botryodiplodin. In: Tetrahedron Letters, 2003, vol. 44, n° 43, p. 7901-7904. https://archive-ouverte.unige.ch/unige:8094

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Deposited on : 2010-06-21

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