Stereocontrolled syntheses of alpha-C-mannosyltryptophan and its analogues.
The total synthesis of alpha-C-mannosyltryptophan (C-Man-Trp), a naturally occurring C-glycosylamino acid, was achieved from a commercially available alpha-methyl-D-mannoside in 10 steps including the following key steps: the C-glycosidation of a mannose derivative with a stannylacetylene, Castro indole synthesis, and Sc(ClO4)3-promoted coupling with L-serine-derived aziridine carboxylate. The glucose- and galactose-analogues of C-Man-Trp were also synthesized in a similar manner. Conformational analyses of the synthesized C-glycosyltryptophan and its synthetic intermediate are briefly discussed.
Nishikawa
Toshio
T
Laboratory of Organic Chemistry, Graduate School of Bioagricultural Sciences, Nagoya University, Chikusa, Nagoya 464-8601, Japan. nisikawa@agr.nagoyya-u.ac.jp
Koide
Yuya
Y
Kajii
Shigeo
S
Wada
Kyoko
K
Ishikawa
Miyuki
M
Isobe
Minoru
M
D001388:Aziridines / Q000737:chemistry; D007211:Indoles / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008766:Methylmannosides / Q000737:chemistry; D008968:Molecular Conformation; D015394:Molecular Structure; D009005:Monosaccharides / Q000737:chemistry; D014364:Tryptophan / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry
D001388:Aziridines; C101500:C(2)-mannosyltryptophan; D007211:Indoles; D008766:Methylmannosides; D009005:Monosaccharides; C008466:methylmannoside; D014364:Tryptophan