Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 53, Issue 2, Pages 512-516Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201308905
Keywords
amides; chemoselectivity; gephyrotoxin; nucleophilic addition; total synthesis
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Funding
- MEXT [24750045]
- Naito Foundation
- JSPS [24.1843]
- Grants-in-Aid for Scientific Research [24750045] Funding Source: KAKEN
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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.
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