Design and Synthesis of Orthogonally Protected d- and l-β-Hydroxyenduracididines from d-lyxono-1,4-Lactone.
A practical synthesis of the orthogonally protected d- and l-β-hydroxyenduracididines (d- and l-βhEnds), the unique, nonproteinogenic α-amino acids found in mannopeptimycin antibiotics, is described. We appropriately applied d-lyxono-1,4-lactone derivatives as a starting template and investigated two transformations: (i) reduction of the lactone in a two-step sequence and (ii) regioselective ring opening of the benzylidene acetal. By careful evaluation of reaction conditions, multigram amounts of both orthogonally protected d- and l-βhEnds were successfully prepared.
Genomics Research Center, Academia Sinica , 128, Section 2, Academia Road, Taipei 11529, Taiwan.
Cheng-Kun
CK
Lin
Genomics Research Center, Academia Sinica , 128, Section 2, Academia Road, Taipei 11529, Taiwan.
Chung-Chien
CC
Hou
Genomics Research Center, Academia Sinica , 128, Section 2, Academia Road, Taipei 11529, Taiwan.
Yi-Yong
YY
Guo
Genomics Research Center, Academia Sinica , 128, Section 2, Academia Road, Taipei 11529, Taiwan.
Wei-Chieh
WC
Cheng