The total synthesis of roquefortine C and a rationale for the thermodynamic stability of isoroquefortine C over roquefortine C.
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.
Shangguan
Ning
N
Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323, USA.
Hehre
Warren J
WJ
Ohlinger
William S
WS
Beavers
Mary Pat
MP
Joullié
Madeleine M
MM
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
D006576:Heterocyclic Compounds, 4 or More Rings; D007093:Imidazoles; D007211:Indoles; D010879:Piperazines; D006639:Histidine; C012536:roquefortine