Literature DB >> 19514728

Syntheses of carbocyclic uracil polyoxin C analogs: application of Pd(0)/InI-allylation of 4-acetoxy-2-azetidinone.

Cara Cesario1, Marvin J Miller.   

Abstract

Carbocyclic uracil polyoxin C analogs are prepared from an acylnitroso-derived hetero Diels-Alder cycloadduct in fewer than nine steps. Pd(0)/InI-mediated allylation of 4-acetoxy-2-azetidinone is used to install the beta-amino acid side chain at the C-5' position of the carbocycle.

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Year:  2009        PMID： 19514728      PMCID： PMC2745051          DOI： 10.1021/jo900861x

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  17 in total

1.  Studies on polyoxins, antifungal antibiotics. 13. The structure of polyoxins.

Authors:  K Isono; K Asahi; S Suzuki
Journal:  J Am Chem Soc       Date:  1969-12-17       Impact factor: 15.419

Review 2.  Carbocyclic nucleosides.

Authors:  V E Marquez; M I Lim
Journal:  Med Res Rev       Date:  1986 Jan-Mar       Impact factor: 12.944

Review 3.  Recent advances in the synthesis of the carbocyclic nucleosides as potential antiviral agents.

Authors:  Lak Shin Jeong; Jeong A Lee
Journal:  Antivir Chem Chemother       Date:  2004-09

4.  Total Synthesis of (+/-) Carbocyclic Polyoxin C and Its alpha-Epimer.

Authors:  Deyi Zhang; Marvin J. Miller
Journal:  J Org Chem       Date:  1998-02-06       Impact factor: 4.354

5.  A novel beta-lactam antibiotic activates tumor cell apoptotic program by inducing DNA damage.

Authors:  David M Smith; Aslamuzzaman Kazi; Lisa Smith; Timothy E Long; Bart Heldreth; Edward Turos; Q Ping Dou
Journal:  Mol Pharmacol       Date:  2002-06       Impact factor: 4.436

6.  Chemoenzymatic synthesis and synthetic application of enantiopure aminocyclopentenols: total synthesis of carbocyclic (+)-uracil polyoxin C and its alpha-epimer.

Authors:  Fangzheng Li; John B Brogan; Jennifer L Gage; Deyi Zhang; Marvin J Miller
Journal:  J Org Chem       Date:  2004-06-25       Impact factor: 4.354

7.  Synthesis and biological activity of tripeptidyl polyoxins as antifungal agents.

Authors:  F Naider; P Shenbagamurthi; A S Steinfeld; H A Smith; C Boney; J M Becker
Journal:  Antimicrob Agents Chemother       Date:  1983-11       Impact factor: 5.191

8.  Synthesis of new polyoxin derivatives and their activity against chitin synthase from Candida albicans.

Authors:  G Emmer; N S Ryder; M A Grassberger
Journal:  J Med Chem       Date:  1985-03       Impact factor: 7.446

9.  Novel N-thiolated beta-lactam antibiotics selectively induce apoptosis in human tumor and transformed, but not normal or nontransformed, cells.

Authors:  Aslamuzzaman Kazi; Randy Hill; Timothy E Long; Deborah J Kuhn; Edward Turos; Q Ping Dou
Journal:  Biochem Pharmacol       Date:  2004-01-15       Impact factor: 5.858

10.  Synthesis and biological evaluation of dipeptidyl and tripeptidyl polyoxin and nikkomycin analogues as anticandidal prodrugs.

Authors:  E Krainer; J M Becker; F Naider
Journal:  J Med Chem       Date:  1991-01       Impact factor: 7.446
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  4 in total

1.  Syntheses of carbocyclic aminonucleosides and (-)-epi-4'-carbocyclic puromycin: Application of palladium(0)/indium iodide-allylations and tethered aminohydroxylations.

Authors:  Cara Cesario; Lawrence P Tardibono; Marvin J Miller
Journal:  Tetrahedron Lett       Date:  2010-06-09       Impact factor: 2.415

2.  Syntheses and Biological Evaluations of Highly Functionalized Hydroxamate Containing and N-Methylthio Monobactams as Anti-Tuberculosis and β-Lactamase Inhibitory Agents.

Authors:  Mark W Majewski; Kyle D Watson; Sanghyun Cho; Patricia A Miller; Scott G Franzblau; Marvin J Miller
Journal:  Medchemcomm       Date:  2015-10-05       Impact factor: 3.597

3.  Cyclopropanation of nitroso Diels-Alder cycloadducts and application to the synthesis of a 2',3'-methano carbocyclic nucleoside.

Authors:  Cheng Ji; Marvin J Miller
Journal:  Tetrahedron Lett       Date:  2010-07-01       Impact factor: 2.415

4.  Enantioselective syntheses of carbocyclic nuleosides 5'-homocarbovir, epi-4'-homocarbovir and their cyclopropylamine analogs using facially selective Pd-mediated allylations.

Authors:  Lawrence P Tardibono; Marvin J Miller; Jan Balzarini
Journal:  Tetrahedron       Date:  2011-02-04       Impact factor: 2.457
  4 in total

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