Borinic acid catalyzed 1, 2-cis-stereoselective glycosylations and their applications to the total synthesis of natural products

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1 Citation (Scopus)

Abstract

In this mini-review article, d (i 4-fluoro) phenylborinic acid ( 3c) catalyzed 1, 2-cis-a and ß - stereoselective glycosylations using 1, 2-anhydroglucose donor 8 and 1, 2-anhydromannose donor 11, respectively, that have recently been developed in our laboratory, are introduced. In addition, representative applications of these glycosylation methods to the stereoselective synthesis of biologically active natural products, GSL-1 and acremomannolipin A, are also introduced.

Original languageEnglish
Pages (from-to)470-473
Number of pages4
JournalYuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
Volume76
Issue number5
DOIs
Publication statusPublished - 2018 Jan 1

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Borinic Acids
Glycosylation
Biological Products
Acids

Keywords

  • 1,2-cis-glycoside
  • Borinic acid
  • Glycosylation
  • Natural glycolipid
  • Stereoselective

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

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title = "Borinic acid catalyzed 1, 2-cis-stereoselective glycosylations and their applications to the total synthesis of natural products",
abstract = "In this mini-review article, d (i 4-fluoro) phenylborinic acid ( 3c) catalyzed 1, 2-cis-a and {\ss} - stereoselective glycosylations using 1, 2-anhydroglucose donor 8 and 1, 2-anhydromannose donor 11, respectively, that have recently been developed in our laboratory, are introduced. In addition, representative applications of these glycosylation methods to the stereoselective synthesis of biologically active natural products, GSL-1 and acremomannolipin A, are also introduced.",
keywords = "1,2-cis-glycoside, Borinic acid, Glycosylation, Natural glycolipid, Stereoselective",
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AB - In this mini-review article, d (i 4-fluoro) phenylborinic acid ( 3c) catalyzed 1, 2-cis-a and ß - stereoselective glycosylations using 1, 2-anhydroglucose donor 8 and 1, 2-anhydromannose donor 11, respectively, that have recently been developed in our laboratory, are introduced. In addition, representative applications of these glycosylation methods to the stereoselective synthesis of biologically active natural products, GSL-1 and acremomannolipin A, are also introduced.

KW - 1,2-cis-glycoside

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KW - Natural glycolipid

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