Chirospecific Synthesis of the (2S,3R)- and (2S,3S)-3-Amino-2-Hydroxy-4-Phenylbutanoic Acids from Sugar: Application to (-)-Bestatin

Jin Hwan Lee; Byong Won Lee; Ki Chang Jang; Ill-Yun Jeong; Min Suk Yang; Sang Gyeong Lee; Ki Hun Park

doi:10.1055/s-2003-38678

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Synthesis 2003(6): 0829-0836
DOI: 10.1055/s-2003-38678

PAPER

Chirospecific Synthesis of the (2S,3R)- and (2S,3S)-3-Amino-2-Hydroxy-4-Phenylbutanoic Acids from Sugar: Application to (-)-Bestatin

Jin Hwan Lee^a, Byong Won Lee^a, Ki Chang Jang^a, Ill-Yun Jeong^a, Min Suk Yang^a, Sang Gyeong Lee^b, Ki Hun Park*^a
^a Department of Agricultural Chemistry, Division of Applied Life Science, Gyeongsang National University, Chinju 660-701, South Korea
Fax: +82(55)7570178; e-Mail: khpark@gshp.gsnu.ac.kr;
^b Department of Chemistry, Gyeongsang National University, Chinju 660-701, South Korea

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Publication History

Received 17 December 2002
Publication Date:
16 April 2003 (online)

Abstract
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Abstract

The enantiomerically pure (2S,3R)- and (2S,3S)-3-amino-2-hydroxy-4-phenylbutanoic acids (AHPBA) were first obtained from sugar in a chirospecific manner. Additionally, the obtained (2S,3R)-AHPBA 1 was easily applied to the synthesis of (-)-bestatin.

Key words

(2S,3R)-AHPBA - (2S,3S)-AHPBA - d-gulonic acid γ-lactone - bestatin - aminopeptidase inhibitor

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The chiral aminoalcohol (19) has been obtained using the same reaction conditions in Scheme [2] .