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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 international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201308905
Subject(s) - amide , electrophile , nucleophile , aldehyde , chemistry , total synthesis , combinatorial chemistry , nucleophilic addition , chemoselectivity , organic chemistry , catalysis
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.