SYNTHESIS OF L-ERYTHRO-ALPHA, BETA-DIHYDROXY-GABA AND GAMMA-HYDROXY-L-ERYTHRONINE BY OXIDATIVE-DEGRADATION OF AMINO-4-PENTENEDIOLS

The regioisomeric epoxy-4-pentenols B and D, readily accessible from 1,4-pentadiene-3-ol A in high stereoisomer purity by Sharpless epoxidation, have been shown to produce various regio- and stereoisomers of amino-4-pentenediols in a controlled manner. The N-protected derivatives of 1- and 3-aminopentenediols 2 and 11, respectively, are suitable for oxidative degradation to amino acid derivatives. Subsequent hydrolysis provides the rare amino-dihydroxy-butyric acid hydrochlorides 9 and 15.