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Concise synthesis of complicated polypropionates through one-pot dissymmetrical two-directional chain elongation.
Journal article

Concise synthesis of complicated polypropionates through one-pot dissymmetrical two-directional chain elongation.

  • Exner CJ Laboratoire de Glycochimie et de Synthèse asymétrique, École Polytechnique Fédérale de Lausanne, 1015 Lausanne, Switzerland.
  • Turks M
  • Fonquerne F
  • Vogel P
  • 2011-03-10
Published in:
  • Chemistry (Weinheim an der Bergstrasse, Germany). - 2011
Alkenes
Molecular Structure
Propionates
Silanes
Stereoisomerism
Sulfur Dioxide
English Herein, a major breakthrough in a sulfur dioxide-mediated oxyallylation cascade reaction is reported that allows the preparation of complex long-chain polyketide fragments with more than ten stereogenic centers through a carefully designed desymmetrization process. An allylbissilane is combined, under the appropriate reaction conditions, with two different 1,3-dioxy-1,3-dienes permitting the construction of a 13-membered polypropionate precursor in one pot. Four stereocenters are selectively created during this process. The so-obtained pseudo-C(2)- or -C(S)-symmetric products are desymmetrized through selective deprotection and can be selectively elongated in both directions using aldol chemistry.
Language
  • English
Open access status
closed
Identifiers
Persistent URL
https://sonar.ch/global/documents/96925
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