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Synfacts 2006(12): 1203-1203
DOI: 10.1055/s-2006-955600
DOI: 10.1055/s-2006-955600
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York
Synthetic Approach to Otamixaban
T. Sakai, Y. Kawamoto, K. Tomioka*
Kyoto University, Japan
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
22. November 2006 (online)
![](https://www.thieme-connect.de/media/synfacts/200612/lookinside/thumbnails/10.1055-s-2006-955600-1.jpg)
Significance
Otamixaban is a lead anticoagulant that inhibits factor Xa, a serine protease implicated in thrombin activation. A salient feature of the synthesis of the key β-amino ester G is an asymmetric conjugate addition of the achiral lithium amide A to ester B in the presence of chiral ligand C. The methyl ester analogue of I has been converted into otamixaban: K. R. Guertin et al. Bioorg. Med. Chem. Lett. 2002, 12, 1671-1674. This report by Tomioka and co-workers was evaluated from a different point of view with the emphasis on metal-mediated synthesis in an earlier issue of Synfacts (Synfacts 2006, 942).