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

K. Tomooka; M. Kikuchi; K. 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

K. Tomooka
, M. Kikuchi
, K. Igawa
, P. H. Keong
, T. Nakai

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

24 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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10.1016/S0040-4039(99)00043-X

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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.",

keywords = "Asymmetric synthesis, Glycosides, Rearrangement, Zaragozic acids",

author = "K. Tomooka and M. Kikuchi and K. Igawa and Keong, \{P. H.\} and T. Nakai",

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T2 - A new approach to the core part of zaragozic acids

AU - Tomooka, K.

AU - Kikuchi, M.

AU - Igawa, K.

AU - Keong, P. H.

AU - Nakai, T.

PY - 1999/3/5

Y1 - 1999/3/5

N2 - 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.

AB - 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.

KW - Asymmetric synthesis

KW - Glycosides

KW - Rearrangement

KW - Zaragozic acids

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UR - https://www.scopus.com/pages/publications/0033525664#tab=citedBy

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 10

ER -

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

Abstract

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