gephyrotoxin and scandium-triflate

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.

Topics: Alkaloids; Amides; Catalysis; Mesylates; Molecular Structure; Oxidation-Reduction; Scandium; Stereoisomerism; Trialkyltin Compounds