Stereoselective Synthesis of (2S,3R)- and (2S,3S)- 2-Amino-3-(3,4-dihydroxyphenyl)-3-hydroxypropanoic Acid
- 1 January 2021
- journal article
- research article
- Published by The Japan Institute of Heterocyclic Chemistry in HETEROCYCLES
- Vol. 103 (2), 965-979
- https://doi.org/10.3987/com-20-s(k)70
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.Keywords
This publication has 27 references indexed in Scilit:
- Scalable Synthesis of the Desoxy-biphenomycin B CoreOrganic Process Research & Development, 2011
- Evolution of the Total Syntheses of Ustiloxin Natural Products and Their AnaloguesJournal of the American Chemical Society, 2008
- The Enantioselective Synthesis of Phomopsin BAngewandte Chemie, 2007
- Enantioselective Total Synthesis of Ustiloxin DJournal of the American Chemical Society, 2003
- Diastereoselective Synthesis of All Stereoisomers of β-Methoxytyrosine, a Component of PapuamidesThe Journal of Organic Chemistry, 2002
- Garner's aldehydeJournal of the Chemical Society, Perkin Transactions 1, 2001
- Practical Synthesis of threo-(S,2S)- and erythro-(1R,2S)-1-Phenyl-2-palmitoylamino-3-morpholino-1-propanol (PPMP) from l-SerineSynlett, 1998
- Selective transformations of threo-2,3-dihydroxy estersThe Journal of Organic Chemistry, 1991
- The X-ray structure of phomopsin A, a hexapeptide mycotoxinJournal of the Chemical Society, Chemical Communications, 1986
- Isolation and antitumor activity of cyclic hexapeptides isolated from Rubiae radix.CHEMICAL & PHARMACEUTICAL BULLETIN, 1984