Stereoselective synthesis of highly functionalized C-glycosides based on acetal [1,2] and [1,4] Wittig rearrangements

Katsuhiko Tomooka, Hiroshi Yamamoto, Takeshi Nakai

Research output: Contribution to journalArticle

35 Citations (Scopus)

Abstract

Two types of highly functionalized C-glycosides were stereoselectively synthesized from an ethynylvinyl-methanol-derived O-glycoside in one step through acetal Wittig rearrangements (see scheme). The [1,2] Wittig rearrangement affords the 1β-C-glycoside that has contiguous quarternary chiral centers at the C1 and C1′ positions, while the [1,4] Wittig rearrangement has been used for the first time in the synthesis of C-glycosides.

Original languageEnglish
Pages (from-to)4500-4502
Number of pages3
JournalAngewandte Chemie - International Edition
Volume39
Issue number24
DOIs
Publication statusPublished - Dec 15 2000

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Glycosides
Acetals
Methanol
C-glycoside

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)

Cite this

Stereoselective synthesis of highly functionalized C-glycosides based on acetal [1,2] and [1,4] Wittig rearrangements. / Tomooka, Katsuhiko; Yamamoto, Hiroshi; Nakai, Takeshi.

In: Angewandte Chemie - International Edition, Vol. 39, No. 24, 15.12.2000, p. 4500-4502.

Research output: Contribution to journalArticle

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