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Total Synthesis of (±)‐Gephyrotoxin by Amide‐Selective Reductive Nucleophilic Addition
Author(s) -
Shirokane Kenji,
Wada Takamasa,
Yoritate Makoto,
Minamikawa Ryo,
Takayama Nobuaki,
Sato Takaaki,
Chida Noritaka
Publication year - 2014
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201308905
Subject(s) - amide , chemistry , electrophile , aldehyde , nucleophile , total synthesis , nucleophilic addition , chemoselectivity , combinatorial chemistry , protecting group , organic chemistry , catalysis , alkyl
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.