Organic and Biomolecular Chemistry p. 687 - 700 (2005)
Update date:2022-09-26
Topics:
Nishikawa, Toshio
Koide, Yuya
Kajii, Shigeo
Wada, Kyoko
Ishikawa, Miyuki
Isobe, Minoru
The total synthesis of α-C-mannosyltryptophan (C-Man-Trp), a naturally occurring C-glycosylamino acid, was achieved from a commercially available α-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.
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(2017)
