title: Novel Synthesis of (-)-Bestatin from L-Aspartic Acid.
abstract: Oxazoline-4-acetate derivative 3 that could be readily obtained from L-aspartic acid was subjected to highly stereoselective hydroxylation, and subsequent Mitsunobu inversion of the hydroxyl group led to (2S,3R)-3-amino-3-benzyl-2-hydroxybutanoic acid derivative 8 in a good yield. Coupling of 8 with L-leucine benzyl ester and subsequent cleavage of the protective groups provided (-)-bestatin 1 in a high yield.
authors.affiliation: a Discovery Research Laboratory, Tanabe Seiyaku Co. Ltd.
authors.forename: M
authors.initials: M
authors.lastname: Seki
authors.affiliation: a Discovery Research Laboratory, Tanabe Seiyaku Co. Ltd.
authors.forename: K
authors.initials: K
authors.lastname: Nakao
keywords: L-aspartic acid; bestatin; diastereoselective hydroxylation; α-hydroxy-β-amino acid