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

Yoshisuke Tsuda, Tomoko Nakamoto, Fumiyuki Kiuchi, Yukihiko Kameda

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Abstract

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
JournalHeterocycles
Volume44
Issue number1
Publication statusPublished - 1997
Externally publishedYes

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Decarboxylation
Cyclization
Methylation
Chemical activation
Derivatives
validamine

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Thiovalidamine derivatives of manno- and gluco-type : Remote activation and anchimeric assistance. / Tsuda, Yoshisuke; Nakamoto, Tomoko; Kiuchi, Fumiyuki; Kameda, Yukihiko.

In: Heterocycles, Vol. 44, No. 1, 1997, p. 427-433.

Research output: Contribution to journalArticle

Tsuda, Yoshisuke ; Nakamoto, Tomoko ; Kiuchi, Fumiyuki ; Kameda, Yukihiko. / Thiovalidamine derivatives of manno- and gluco-type : Remote activation and anchimeric assistance. In: Heterocycles. 1997 ; Vol. 44, No. 1. pp. 427-433.
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