916582-47-3Relevant articles and documents
Total synthesis of (±)-gephyrotoxin by amide-selective reductive nucleophilic addition
Shirokane, Kenji,Wada, Takamasa,Yoritate, Makoto,Minamikawa, Ryo,Takayama, Nobuaki,Sato, Takaaki,Chida, Noritaka
supporting information, p. 512 - 516 (2014/01/23)
A chemoselective approach for the total synthesis of (±)- gephyrotoxin has been developed. The key to success was the utilization of N-methoxyamides, which enabled the direct coupling of the amide with an aldehyde and selective reductive nucleophilic addition to the amide in the presence of a variety of sensitive and electrophilic functional groups, such as a methyl ester. This chemoselective approach minimized the use of protecting-group manipulations and redox reactions, which resulted in the most concise and efficient total synthesis of (±)-gephyrotoxin described to date. Aim for selectivity: A chemoselective approach that utilizes N-methoxyamides has been developed for the total synthesis of (±)-gephyrotoxin. The N-methoxy group enabled the direct coupling of the amide with an aldehyde and amide-selective reductive allylation in the presence of a more electrophilic methyl ester, which resulted in the most concise and efficient total synthesis of (±)-gephyrotoxin described to date.
