Asymmetric total synthesis of trilobacin via organoselenium-mediated oxonium ion formation/SiO2-promoted fragmentation.
An asymmetric total synthesis of trilobacin (1), an annonaceous acetogenin with potent anticancer activities, was accomplished wherein the construction of its erythro-bis(2,2')-tetrahydrofuran core 2 featured a novel organoselenium-mediated oxonium ion formation/SiO(2)-promoted fragmentation of alpha,alpha'-cis-oxocene 3.
Sohn
Te-ik
TI
College of Pharmacy, Seoul National University, Seoul 151-742, Korea.
Kim
Mi Jung
MJ
Kim
Deukjoon
D
D003500:Cyclization; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D007477:Ions / Q000737:chemistry; D008968:Molecular Conformation; D016566:Organoselenium Compounds / Q000737:chemistry*; D035964:Oxocins / Q000737:chemistry*; D012822:Silicon Dioxide / Q000737:chemistry*; D013237:Stereoisomerism
D005663:Furans; D007477:Ions; D016566:Organoselenium Compounds; D035964:Oxocins; C074719:trilobacin; D012822:Silicon Dioxide