The Total Synthesis of Roquefortine C and a Rationale for the Thermodynamic Stability of Isoroquefortine C over Roquefortine C

Ning Shangguan, Warren J. Hehre, William S. Ohlinger, Mary Pat Beavers, Madeleine M. Joullié
Wavefunction, Inc., 18401 Von Karman Avenue, Suite 370, Irvine, California 92612, Institute for Medicine and Engineering, University of Pennsylvania, 1026 Vagelos Research Labs, Philadelphia, Pennsylvania 19104-6383, and Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323
J. Am. Chem. Soc., 2008, 130 (19), pp 6281–6287
DOI: 10.1021/ja800067q
Publication Date (Web): April 16, 2008
Copyright © 2008 American Chemical Society

Abstract

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The first total synthesis of roquefortine C is achieved by implementation of a novel elimination strategy to construct the thermodynamically unstable E-dehydrohistidine moiety. Molecular modeling studies are presented which explain the instability of the roquefortine C structure compared to that of isoroquefortine C.

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History

  • Published In Issue May 14, 2008
  • Article ASAPApril 16, 2008
  • Received: January 04, 2008

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