Literature DB >> 24889256

Asymmetric stereodivergent strategy towards aminocyclitols.

Barry M Trost1, Sushant Malhotra.   

Abstract

A concise asymmetric synthesis of aminocyclitols, such as diastereomeric 2-deoxystreptamine analogues and conduramine A, is described. The Pd-catalyzed asymmetric desymmetrization of meso 1,4-dibenzolate enables the synthesis of highly oxidized cyclohexane architectures. These scaffolds can potentially be used to access new aminoglycoside antibiotics and enantiomerically pure α-glucosidase inhibitors.
© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  aminoglycoside; azidization; conduramines; palladium; synthetic methods

Mesh：

Substances：

Year:  2014        PMID： 24889256      PMCID： PMC4237701          DOI： 10.1002/chem.201402175

Source DB:  PubMed          Journal:  Chemistry        ISSN： 0947-6539            Impact factor:   5.236


  13 in total

Review 1.  Aminoglycosides: perspectives on mechanisms of action and resistance and strategies to counter resistance.

Authors:  L P Kotra; J Haddad; S Mobashery
Journal:  Antimicrob Agents Chemother       Date:  2000-12       Impact factor: 5.191

2.  Structure-based design, synthesis and A-site rRNA co-crystal complexes of novel amphiphilic aminoglycoside antibiotics with new binding modes: a synergistic hydrophobic effect against resistant bacteria.

Authors:  Stephen Hanessian; Kandasamy Pachamuthu; Janek Szychowski; Alexandre Giguère; Eric E Swayze; Michael T Migawa; Boris François; Jiro Kondo; Eric Westhof
Journal:  Bioorg Med Chem Lett       Date:  2010-09-19       Impact factor: 2.823

3.  Novel acyclic deoxystreptamine mimetics targeting the ribosomal decoding site.

Authors:  Dionisios Vourloumis; Geoffrey C Winters; Masayuki Takahashi; Klaus B Simonsen; Benjamin K Ayida; Sarah Shandrick; Qiang Zhao; Thomas Hermann
Journal:  Chembiochem       Date:  2003-09-05       Impact factor: 3.164

Review 4.  2-Deoxystreptamine: central scaffold of aminoglycoside antibiotics.

Authors:  Guuske F Busscher; Floris P J T Rutjes; Floris L van Delft
Journal:  Chem Rev       Date:  2005-03       Impact factor: 60.622

5.  Design of novel antibiotics that bind to the ribosomal acyltransfer site.

Authors:  Jalal Haddad; Lakshmi P Kotra; Beatriz Llano-Sotelo; Choonkeun Kim; Eduardo F Azucena; Meizheng Liu; Sergei B Vakulenko; Christine S Chow; Shahriar Mobashery
Journal:  J Am Chem Soc       Date:  2002-04-03       Impact factor: 15.419

6.  BB-K 8, a new semisynthetic aminoglycoside antibiotic.

Authors:  H Kawaguchi; T Naito; S Nakagawa; K I Fujisawa
Journal:  J Antibiot (Tokyo)       Date:  1972-12       Impact factor: 2.649

Review 7.  Versatility of aminoglycosides and prospects for their future.

Authors:  Sergei B Vakulenko; Shahriar Mobashery
Journal:  Clin Microbiol Rev       Date:  2003-07       Impact factor: 26.132

Review 8.  Biosynthesis of unusual aminocyclitol-containing natural products.

Authors:  Taifo Mahmud; Patricia M Flatt; Xiumei Wu
Journal:  J Nat Prod       Date:  2007-07-28       Impact factor: 4.050

9.  Rational design of azepane-glycoside antibiotics targeting the bacterial ribosome.

Authors:  Sofia Barluenga; Klaus B Simonsen; Ethel S Littlefield; Benjamin K Ayida; Dionisios Vourloumis; Geoffrey C Winters; Masayuki Takahashi; Sarah Shandrick; Qiang Zhao; Qing Han; Thomas Hermann
Journal:  Bioorg Med Chem Lett       Date:  2004-02-09       Impact factor: 2.823

Review 10.  Aminoglycosides: nephrotoxicity.

Authors:  M P Mingeot-Leclercq; P M Tulkens
Journal:  Antimicrob Agents Chemother       Date:  1999-05       Impact factor: 5.191
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  1 in total

1.  Synthesis of (+)-ribostamycin by catalytic, enantioselective hydroamination of benzene.

Authors:  Chad N Ungarean; Petra Galer; Yu Zhang; Ken S Lee; Justin M Ngai; Sungjong Lee; Peng Liu; David Sarlah
Journal:  Nat Synth       Date:  2022-05-26
  1 in total

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