Divergent approach to imino sugar C-glycosides using imino glycals: Application to the stereocontrolled synthesis of (+)-deoxoprosophylline

Paul J. Dransfield; Paul M. Gore; Michael Shipman; Alexandra M.Z. Slawin

doi:10.1039/b110035a

Divergent approach to imino sugar C-glycosides using imino glycals: Application to the stereocontrolled synthesis of (+)-deoxoprosophylline

Paul J. Dransfield, Paul M. Gore, Michael Shipman, Alexandra M.Z. Slawin

School of Chemistry

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

Abstract

Tri-O-acetyl imino glucal 2 is readily made and shown to undergo a variety of Lewis acid mediated carbon-carbon bond forming reactions at C-1 of the piperidine nucleus. In all the reactions studied, the β-anomer is predominant.

Original language	English
Pages (from-to)	150-151
Number of pages	2
Journal	Chemical Communications
Volume	2
DOIs	https://doi.org/10.1039/b110035a
Publication status	Published - 21 Jan 2002

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title = "Divergent approach to imino sugar C-glycosides using imino glycals: Application to the stereocontrolled synthesis of (+)-deoxoprosophylline",

abstract = "Tri-O-acetyl imino glucal 2 is readily made and shown to undergo a variety of Lewis acid mediated carbon-carbon bond forming reactions at C-1 of the piperidine nucleus. In all the reactions studied, the β-anomer is predominant.",

author = "Dransfield, \{Paul J.\} and Gore, \{Paul M.\} and Michael Shipman and Slawin, \{Alexandra M.Z.\}",

year = "2002",

month = jan,

day = "21",

doi = "10.1039/b110035a",

language = "English",

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pages = "150--151",

journal = "Chemical Communications",

issn = "1359-7345",

publisher = "Royal Society of Chemistry",

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T1 - Divergent approach to imino sugar C-glycosides using imino glycals

T2 - Application to the stereocontrolled synthesis of (+)-deoxoprosophylline

AU - Dransfield, Paul J.

AU - Gore, Paul M.

AU - Shipman, Michael

AU - Slawin, Alexandra M.Z.

PY - 2002/1/21

Y1 - 2002/1/21

N2 - Tri-O-acetyl imino glucal 2 is readily made and shown to undergo a variety of Lewis acid mediated carbon-carbon bond forming reactions at C-1 of the piperidine nucleus. In all the reactions studied, the β-anomer is predominant.

AB - Tri-O-acetyl imino glucal 2 is readily made and shown to undergo a variety of Lewis acid mediated carbon-carbon bond forming reactions at C-1 of the piperidine nucleus. In all the reactions studied, the β-anomer is predominant.

UR - https://www.scopus.com/pages/publications/0037148070

U2 - 10.1039/b110035a

DO - 10.1039/b110035a

M3 - Article

C2 - 12120347

AN - SCOPUS:0037148070

SN - 1359-7345

VL - 2

SP - 150

EP - 151

JO - Chemical Communications

JF - Chemical Communications

ER -

Divergent approach to imino sugar C-glycosides using imino glycals: Application to the stereocontrolled synthesis of (+)-deoxoprosophylline

Abstract

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