Stereoselective synthesis of (2s,3r)- And (2s,3s)-2-amino-3-(3,4-dihydroxyphenyl)-3-hydroxypropanoic acid

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

Research output: Contribution to journalArticlepeer-review

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.

Original languageEnglish
JournalHeterocycles
Volume103
Issue number2
DOIs
Publication statusPublished - 2021

All Science Journal Classification (ASJC) codes

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

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