Total Synthesis of Lacosamide

Total Synthesis of Lacosamide

Total synthesis of anticonvulsant amino acid, lacosamide, is reported. The key step is stereospecific allyl cyanate-to-isocyanate rearrangement, which proceeds with chirality transfer. The enantiopure starting material for the rearrangement step was accessed from ethyl l-lactate.

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Veröffentlicht in:Journal of organic chemistry 2014-07, Vol.79 (13), p.6342-6346
1. Verfasser: Stecko, Sebastian
Format: Artikel
Sprache:eng
Schlagworte:
Acetamides - chemical synthesis
Acetamides - chemistry
Allyl Compounds - chemistry
Amino Acids - chemical synthesis
Amino Acids - chemistry
Anticonvulsants - chemical synthesis
Anticonvulsants - chemistry
Cyanates - chemistry
Isocyanates - chemistry
Lactates - chemistry
Molecular Structure
Stereoisomerism
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Zusammenfassung:Total synthesis of anticonvulsant amino acid, lacosamide, is reported. The key step is stereospecific allyl cyanate-to-isocyanate rearrangement, which proceeds with chirality transfer. The enantiopure starting material for the rearrangement step was accessed from ethyl l-lactate.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo500857t