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

Andrey, Olivier; Vidonne, Annick; Alexakis, Alexandre

doi:10.1016/j.tetlet.2003.09.017

Scientific article

Letter

English

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

ContributorsAndrey, Olivier; Vidonne, Annick; Alexakis, Alexandre

Published inTetrahedron letters, vol. 44, no. 43, p. 7901-7904

Publication date2003

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.

Affiliation

Faculté des sciences / Section de chimie et biochimie / Département de chimie organique

Citation (ISO format)

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. doi: 10.1016/j.tetlet.2003.09.017

Article (Published version)

Identifiers

PID : unige:8094
DOI : 10.1016/j.tetlet.2003.09.017

ISSN of the journal0040-4039

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

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