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

20 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

Access to Document

10.1016/S0040-4039(99)00043-X

Cite this

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

@article{b25be76338914b6a9a0d73010f5be3fa,

title = "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 = "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.",

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

year = "1999",

month = mar,

day = "5",

doi = "10.1016/S0040-4039(99)00043-X",

language = "English",

volume = "40",

pages = "1917--1920",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

number = "10",

}

TY - JOUR

T1 - Stereochemical features of the [1,2]-Wittig rearrangement of O- glycosides derived from D-galactono- and D-xylono-γ-lactones

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

AU - Tomooka, Katsuhiko

AU - Kikuchi, M.

AU - Igawa, Kazunobu

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.

UR - http://www.scopus.com/inward/record.url?scp=0033525664&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0033525664&partnerID=8YFLogxK

U2 - 10.1016/S0040-4039(99)00043-X

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

M3 - Article

AN - SCOPUS:0033525664

VL - 40

SP - 1917

EP - 1920

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

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

All Science Journal Classification (ASJC) codes

Access to Document

Other files and links

Fingerprint

Cite this