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The total synthesis of roquefortine C and a rationale for the thermodynamic stability of isoroquefortine C over roquefortine C.

Shangguan N, Hehre WJ, Ohlinger WS, Beavers MP, Joullié MM

Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323, USA.

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.

Published 7 May 2008 in J Am Chem Soc, 130(19): 6281-7.
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