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

• DOI: 10.1002/ange.201308905
• Publication Date: 2013-11-29T09:26:58Z
• Authors: Kenji Shirokane; Takamasa Wada; Makoto Yoritate; Ryo Minamikawa; Nobuaki Takayama; Takaaki Sato; Noritaka Chida
• Keywords: Amide; Nucleophilic Addition; Chemoselectivity; Protecting group

Abstract A chemoselective approach for the total synthesis of (±)‐gephyrotoxin has been developed. The key to success was utilization N ‐methoxyamides, which enabled direct coupling amide with an aldehyde and selective reductive nucleophilic addition in presence a variety sensitive electrophilic functional groups, such as methyl ester. This minimized use protecting‐group manipulations redox reactions, resulted most concise efficient described date.