Stereochemical features of the [1,2]-Wittig rearrangement of O- glycosides derived from D-galactono- and D-xylono-γ-lactones: A new approach to the core part of zaragozic acids

Katsuhiko Tomooka, M. Kikuchi, Kazunobu Igawa, P. H. Keong, T. Nakai

Research output: Contribution to journalArticlepeer-review

19 Citations (Scopus)

Abstract

The Wittig rearrangement of D-galactono-γ-lactone derived β-O- glycoside is shown to afford β-C-glycoside (retention product), a potentially useful intermediate for zaragozic acid synthesis. By contrast, the rearrangement of the D-xylonolactone-derived counterpart was found to violate the retention principle to yield an inversion product as the major product.

Original languageEnglish
Pages (from-to)1917-1920
Number of pages4
JournalTetrahedron Letters
Volume40
Issue number10
DOIs
Publication statusPublished - Mar 5 1999
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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