Bioscience, Biotechnology, and Biochemistry
Online ISSN : 1347-6947
Print ISSN : 0916-8451
Organic Chemistry Notes
Novel Synthesis of (−)-Bestatin from L-Aspartic Acid
Masahiko SEKIKazuya NAKAO
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JOURNALS FREE ACCESS

1999 Volume 63 Issue 7 Pages 1304-1307

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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.

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© 1999 by Japan Society for Bioscience, Biotechnology, and Agrochemistry
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