Stereoselective Synthesis of (2S,3R)- and (2S,3S)- 2-Amino-3-(3,4-dihydroxyphenyl)-3-hydroxypropanoic Acid

Abstract

Dedicated to Professor Yasuyuki Kita on cerebration on his 77th birthday Abstract -(2S,3R)-and (2S,3S)-2-amino-3-(3,4-dihydroxyphenyl)-3hydroxypropanoic 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.