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

doi:10.1021/ja800067q

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

J Am Chem Soc. 2008 May 14;130(19):6281-7. doi: 10.1021/ja800067q. Epub 2008 Apr 16.

Authors

Ning Shangguan¹, Warren J Hehre, William S Ohlinger, Mary Pat Beavers, Madeleine M Joullié

Affiliation

¹ Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323, USA.

PMID: 18412344
DOI: 10.1021/ja800067q

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.

Publication types

Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

Ascomycota / chemistry
Heterocyclic Compounds, 4 or More Rings / chemical synthesis
Heterocyclic Compounds, 4 or More Rings / chemistry
Histidine / analogs & derivatives
Histidine / chemistry
Hydrogen Bonding
Imidazoles / chemical synthesis
Imidazoles / chemistry
Indoles / chemical synthesis*
Indoles / chemistry
Models, Molecular
Molecular Conformation
Piperazines / chemical synthesis
Piperazines / chemistry
Thermodynamics

Substances

Heterocyclic Compounds, 4 or More Rings
Imidazoles
Indoles
Piperazines
Histidine
roquefortine