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

doi:10.1016/S0040-4039(99)00043-X

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 journal › Article › peer-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 language	English
Pages (from-to)	1917-1920
Number of pages	4
Journal	Tetrahedron Letters
Volume	40
Issue number	10
DOIs	https://doi.org/10.1016/S0040-4039(99)00043-X
Publication status	Published - Mar 5 1999
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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

In: Tetrahedron Letters, Vol. 40, No. 10, 05.03.1999, p. 1917-1920.

Research output: Contribution to journal › Article › peer-review

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