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

J. Am. Chem. Soc., 130 (19), 6281–6287, 2008. 10.1021/ja800067q
Web Release Date: April 16, 2008

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,^‡ and 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

mjoullie@sas.upenn.edu

Received January 4, 2008

Abstract:

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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