Enantioselective synthesis of (2S,3R)-3-hydroxy-3-methylproline, a novel amino acid found in polyoxypeptins.
The enantioselective synthesis of (2S,3R)-3-hydroxy-3-methylproline (3) was achieved by the Sharpless AD, regioselective opening of cyclic sulfate by NaN(3) and intramolecular ring-closing reaction. The reported route has the advantage of a high overall yield and good enantiomeric purity, as well as starting from readily available chemical substrates and inexpensive reagents.
Qin
Dong-Guang
DG
State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, 354 Fenglin Road, Shanghai 200032, China.
Zha
Hui-Yan
HY
Yao
Zhu-Jun
ZJ
D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D013058:Mass Spectrometry; D019906:Nuclear Magnetic Resonance, Biomolecular; D011392:Proline / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
C449928:(2,3)-3-hydroxy-3-methylproline; D000596:Amino Acids; D011392:Proline