Enantioselective synthesis of alpha-methyl-D-cysteine and lanthionine building blocks via alpha-methyl-D-serine-beta-lactone.
[reaction: see text] We report here the enantioselective synthesis of Boc-alpha-methyl-d-cysteine(PMB)-OH and lanthionine building blocks through the regioselective ring opening of key intermediate Boc-alpha-methyl-d-serine-beta-lactone.
Smith
Nicole D
ND
Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, California 92093-0343, USA.
Goodman
Murray
M
D000409:Alanine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D003545:Cysteine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation; D015394:Molecular Structure; D012694:Serine / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry; D013440:Sulfides
D007783:Lactones; D013440:Sulfides; C476502:alpha-methyl-D-serine-beta-lactone; D012694:Serine; C001520:lanthionine; D003545:Cysteine; D000409:Alanine