Asymmetric total synthesis of nigerone.

Org Lett

Department of Chemistry, Roy and Diana Vagelos Laboratories, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323, USA.

Published: February 2007

AI Article Synopsis

  • The chiral bisnaphthopyrone natural product nigerone was synthesized enantioselectively through a detailed chemical process.
  • A critical part of the synthesis involved an eight-step isomerization to achieve nigerone.
  • The isomerization precursor was created using asymmetric oxidative biaryl coupling with a specific 1,5-diaza-cis-decalin copper catalyst.

Article Abstract

[reaction: see text] An enantioselective synthesis of the chiral bisnaphthopyrone natural product nigerone is reported. The key step was an eight-step isomerization process to form the final natural product. The isomerization precursor was constructed via asymmetric oxidative biaryl coupling of an advanced intermediate with a 1,5-diaza-cis-decalin copper catalyst.

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Source
http://dx.doi.org/10.1021/ol062468yDOI Listing

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