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Paper | Special issue | Vol 103, No. 2, 2021, pp.965-979
Published online, 9th March, 2021
DOI: 10.3987/COM-20-S(K)70
Stereoselective Synthesis of (2S,3R)- and (2S,3S)- 2-Amino-3-(3,4-dihydroxyphenyl)-3-hydroxypropanoic Acid

Yoko Yasuno, Shunsuke Yamaguchi, Yuma Karita, Kenta Sakai, Hironori Okamura, Atsushi Nakayama, and Tetsuro Shinada*

*Graduate School of Science, Osaka City University, Sugimoto, Sumiyoshi-ku, Osaka 558-8585, Japan

Abstract

(2S,3R)- and (2S,3S)-2-amino-3-(3,4-dihydroxyphenyl)-3-
hydroxypropanoic acids
(ADHP) are often found in an unusual amino acid component of phomopsin B, ustiloxins, RA-IV, and MPC1001B. Herein, we would like to report stereoselective synthesis of (2S,3R)- and (2S,3S)-ADHP equivalents for the synthesis of ADHP containing natural products. The synthesis is characterized by the stereocontrolled construction of the (2S,3R)- and (2S,3S)-stereocenters starting from Garner’s aldehyde as a common starting material.