Total Synthesis of (±)??Gephyrotoxin by Amide??Selective Reductive Nucleophilic Addition

…, R Minamikawa, N Takayama, T Sato…

Index: Shirokane, Kenji; Wada, Takamasa; Yoritate, Makoto; Minamikawa, Ryo; Takayama, Nobuaki; Sato, Takaaki; Chida, Noritaka Angewandte Chemie - International Edition, 2014 , vol. 53, # 2 p. 512 - 516 Angew. Chem., 2014 , vol. 126, # 2 p. 522 - 526,5

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Citation Number: 35

Abstract

Abstract 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- ...