Total synthesis of (-)-agelastatin A.
A new route to (-)-agelastatin A is reported. The requisite nitrogen functionalities of the agelastatin core have been installed by intramolecular aziridination of an azidoformate and subsequent regioselective azidation, leading to net trans-diamination of the double bond. The present synthesis also demonstrates two new protocols for the preparation of an imidazolidinone hemiaminal motif from an oxazolidinone intermediate which comprise sequential N-tert-butoxycarbonylation, urea formation, hydrolysis, and oxidative cyclization, and direct aminolysis and subsequent oxidative cyclization.
Yoshimitsu
Takehiko
T
Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamadaoka, Suita, Osaka 565-0871, Japan. yoshimit@phs.osaka-u.ac.jp
Ino
Tatsunori
T
Tanaka
Tetsuaki
T
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D007093:Imidazoles / Q000737:chemistry; D007659:Ketones / Q000737:chemistry; D007769:Lactams / Q000737:chemistry; D009584:Nitrogen / Q000737:chemistry; D023303:Oxazolidinones / Q000138:chemical synthesis* / Q000737:chemistry
D000470:Alkaloids; D007093:Imidazoles; D007659:Ketones; D007769:Lactams; D023303:Oxazolidinones; C464968:agelastatin A; C029899:imidazole; D009584:Nitrogen