Thiovalidamine derivatives of manno- and gluco-type: Remote activation and anchimeric assistance

Yoshisuke Tsuda, Tomoko Nakamoto, Fumiyuki Kiuchi, Yukihiko Kameda

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The oxazolidone (3) derived from validamine (1) was dithiocarbonylated, on treatment with NaH followed by CS2-Mel, to the N,O-dicarbodithioate (6). On treatment with NaH-Mel, this afforded the manno-type thiovalidamine derivative (7) and then the gluco-type thiovalidamine derivative (8) following the pathway shown in Scheme 2: an activation at a C=S group by methylation, transferring this activation to a remote position accompanied with decarboxylation, and cyclization of the neighboring group to the transferred position (C-3).

Original languageEnglish
Pages (from-to)427-433
Number of pages7
Issue number1
Publication statusPublished - 1997 Jan 1


ASJC Scopus subject areas

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

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