title: The total synthesis of roquefortine C and a rationale for the thermodynamic stability of isoroquefortine C over roquefortine C.
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.
authors.affiliation: Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323, USA.
authors.forename: Ning
authors.initials: N
authors.lastname: Shangguan
authors.forename: Warren J
authors.initials: WJ
authors.lastname: Hehre
authors.forename: William S
authors.initials: WS
authors.lastname: Ohlinger
authors.forename: Mary Pat
authors.initials: MP
authors.lastname: Beavers
authors.forename: Madeleine M
authors.initials: MM
authors.lastname: Joullié
mesh_terms: D001203:Ascomycota / Q000737:chemistry; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis / Q000737:chemistry; D006639:Histidine / Q000031:analogs & derivatives / Q000737:chemistry; D006860:Hydrogen Bonding; D007093:Imidazoles / Q000138:chemical synthesis / Q000737:chemistry; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D008968:Molecular Conformation; D010879:Piperazines / Q000138:chemical synthesis / Q000737:chemistry; D013816:Thermodynamics
chemical_list: D006576:Heterocyclic Compounds, 4 or More Rings; D007093:Imidazoles; D007211:Indoles; D010879:Piperazines; D006639:Histidine; C012536:roquefortine