M. Hatanaka, N. Noguchi, T. Ishimaru
Apr 1, 1982
Citations
0
Influential Citations
10
Citations
Journal
Bulletin of the Chemical Society of Japan
Abstract
A short and high-yielding synthesis of optically active 3-aminonocardicinic acid (3-ANA) is described. The fourth component condensation reaction of N2-protected L-2,3-diaminopropanoic acid with p-benzyloxybenzaldehyde and butyl isocyanide gave directly the amide derivatives of 3-ANA, as a diastereomeric mixture, which was, after conversion of the amide group into the benzhydryl ester, led in good yield to a single disatereomer with natural chirality via epimerization. Deprotection of the 3-ANA derivative gave 3-ANA.