Literature DB >> 11869118

Stereoselective synthesis of vancosamine and saccharosamine glycals via tungsten-catalyzed alkynol cycloisomerization.

William W Cutchins1, Frank E McDonald.   

Abstract

[reaction: see text] A stereoselective synthesis of the C-3 branched amino glycals of vancosamine and saccharosamine is described that features a tungsten carbonyl catalyzed cycloisomerization of the corresponding alkynyl alcohol.

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Year:  2002        PMID： 11869118     DOI： 10.1021/ol017195f

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  10 in total

1.  Fischer carbene catalysis of alkynol cycloisomerization: application to the synthesis of the altromycin B disaccharide.

Authors:  Bonsuk Koo; Frank E McDonald
Journal:  Org Lett       Date:  2007-03-27       Impact factor: 6.005

2.  Total synthesis of isokidamycin.

Authors:  B Michael O'Keefe; Douglas M Mans; David E Kaelin; Stephen F Martin
Journal:  J Am Chem Soc       Date:  2010-11-10       Impact factor: 15.419

3.  Automated, Multistep Continuous-Flow Synthesis of 2,6-Dideoxy and 3-Amino-2,3,6-trideoxy Monosaccharide Building Blocks.

Authors:  Subbarao Yalamanchili; Tu-Anh Nguyen; Alexander Zsikla; Gavin Stamper; Ashley E DeYong; John Florek; Olivea Vasquez; Nicola L B Pohl; Clay S Bennett
Journal:  Angew Chem Int Ed Engl       Date:  2021-09-21       Impact factor: 16.823

4.  Reagent-Controlled α-Selective Dehydrative Glycosylation of 2,6-Dideoxy Sugars: Construction of the Arugomycin Tetrasaccharide.

Authors:  Joseph R Romeo; Luca McDermott; Clay S Bennett
Journal:  Org Lett       Date:  2020-04-13       Impact factor: 6.005

5.  Brønsted acid-promoted glycosylations of disaccharide glycal substructures of the saccharomicins.

Authors:  Bradley R Balthaser; Frank E McDonald
Journal:  Org Lett       Date:  2009-11-05       Impact factor: 6.005

Review 6.  Metal vinylidenes as catalytic species in organic reactions.

Authors:  Barry M Trost; Andrew McClory
Journal:  Chem Asian J       Date:  2008-02-01

7.  Stereo- and regioselective glycosylations to the bis-C-arylglycoside of kidamycin.

Authors:  ZhongBo Fei; Frank E McDonald
Journal:  Org Lett       Date:  2007-08-11       Impact factor: 6.005

8.  Stereospecific Synthesis of the Saccharosamine-Rhamnose-Fucose Fragment Present in Saccharomicin B.

Authors:  Marissa Bylsma; Clay S Bennett
Journal:  Org Lett       Date:  2018-07-17       Impact factor: 6.005

9.  Rapid de Novo Preparation of 2,6-Dideoxy Sugar Libraries through Gold-Catalyzed Homopropargyl Orthoester Cyclization.

Authors:  Subbarao Yalamanchili; William Miller; Xizhao Chen; Clay S Bennett
Journal:  Org Lett       Date:  2019-11-22       Impact factor: 6.005

10.  Stereodivergent approach in the protected glycal synthesis of L-vancosamine, L-saccharosamine, L-daunosamine and L-ristosamine involving a ring-closing metathesis step.

Authors:  Pierre-Antoine Nocquet; Aurélie Macé; Frédéric Legros; Jacques Lebreton; Gilles Dujardin; Sylvain Collet; Arnaud Martel; Bertrand Carboni; François Carreaux
Journal:  Beilstein J Org Chem       Date:  2018-11-29       Impact factor: 2.883
  10 in total

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