Literature DB >> 16408898

De novo asymmetric synthesis of homoadenosine via a palladium-catalyzed N-glycosylation.

Sanjeeva R Guppi1, Maoquan Zhou, George A O'Doherty.   

Abstract

[reaction: see text] A highly stereoselective synthesis of l-2-deoxy-beta-ribo-hexopyranosyl nucleosides from 6-chloropurine and Boc-protected pyranone has been developed. Our approach relies on the iterative application of a palladium-catalyzed N-glycosylation, diastereoselective reduction, and reductive 1,3-transposition. This strategy is amenable to prepare various natural and unnatural hexopyranosyl nucleosides analogues.

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Year:  2006        PMID： 16408898      PMCID： PMC2546502          DOI： 10.1021/ol052664p

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


  13 in total

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Authors:  Andrew G. Myers; Bin Zheng; Mohammad Movassaghi
Journal:  J Org Chem       Date:  1997-10-17       Impact factor: 4.354

2.  de novo asymmetric synthesis of daumone via a palladium-catalyzed glycosylation.

Authors:  Haibing Guo; George A O'doherty
Journal:  Org Lett       Date:  2005-09-01       Impact factor: 6.005

3.  Total synthesis of Gougerotin.

Authors:  K A Watanabe; E A Falco; J J Fox
Journal:  J Am Chem Soc       Date:  1972-05-03       Impact factor: 15.419

4.  A new antiviral antibiotic SF-2140 produced by Actinomadura.

Authors:  T Ito; K Ohba; M Koyama; M Sezaki; H Tohyama; T Shomura; H Fukuyasu; Y Kazuno; T Niwa; M Kojima
Journal:  J Antibiot (Tokyo)       Date:  1984-08       Impact factor: 2.649

5.  Is there a generalized reverse anomeric Effect? substituent and solvent effects on the configurational equilibria of neutral and protonated N-arylglucopyranosylamines and N-aryl-5-thioglucopyranosylamines

Authors: 
Journal:  J Org Chem       Date:  2000-01-14       Impact factor: 4.354

6.  Chemo-, regio-, and enantioselective Pd-catalyzed allylic alkylation of indolocarbazole pro-aglycons.

Authors:  Barry M Trost; Michael J Krische; Volker Berl; Ellen M Grenzer
Journal:  Org Lett       Date:  2002-06-13       Impact factor: 6.005

7.  Synthesis, structure, and biological activity of certain 2-deoxy-beta-D-ribo-hexopyranosyl nucleosides and nucleotides.

Authors:  L D Nord; N K Dalley; P A McKernan; R K Robins
Journal:  J Med Chem       Date:  1987-06       Impact factor: 7.446

8.  A palladium-catalyzed glycosylation reaction: the de novo synthesis of natural and unnatural glycosides.

Authors:  Ravula Satheesh Babu; George A O'Doherty
Journal:  J Am Chem Soc       Date:  2003-10-15       Impact factor: 15.419

9.  De novo synthesis of oligosaccharides using a palladium-catalyzed glycosylation reaction.

Authors:  Ravula Satheesh Babu; Maoquan Zhou; George A O'Doherty
Journal:  J Am Chem Soc       Date:  2004-03-24       Impact factor: 15.419

10.  Bagougeramines A and B, new nucleoside antibiotics produced by a strain of Bacillus circulans. II. Physico-chemical properties and structure determination.

Authors:  A Takahashi; D Ikeda; H Naganawa; Y Okami; H Umezawa
Journal:  J Antibiot (Tokyo)       Date:  1986-08       Impact factor: 2.649
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  3 in total

1.  De novo asymmetric syntheses of SL0101 and its analogues via a palladium-catalyzed glycosylation.

Authors:  Mingde Shan; George A O'Doherty
Journal:  Org Lett       Date:  2006-10-26       Impact factor: 6.005

Review 2.  Synthesis and biological study of the phomopsolide and phomopsolidone natural products.

Authors:  Alhanouf Z Aljahdali; Kathryn A Foster; George A O'Doherty
Journal:  Chem Commun (Camb)       Date:  2020-10-07       Impact factor: 6.222

3.  Synthesis of aza-analogues of the glycosylated tyrosine portion of mannopeptimycin-E.

Authors:  Sanjeeva R Guppi; George A O'Doherty
Journal:  J Org Chem       Date:  2007-05-26       Impact factor: 4.354
  3 in total

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