Literature DB >> 20640052

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

Cara Cesario1, Lawrence P Tardibono, Marvin J Miller.   

Abstract

Carbocyclic aminonucleosides and epi-4'-carbocyclic puromycin were prepared from an acylnitroso-derived hetero Diels-Alder cycloadduct. Pd(0)/InI-mediated allylations of a formyl species were used to install the 4'-hydroxymethyl group. A tethered aminohydroxylation strategy was employed to install the cis-2',3'-aminoalcohol moiety with complete regio- and diastereocontrol.

Entities:  

Year:  2010        PMID： 20640052      PMCID： PMC2903068          DOI： 10.1016/j.tetlet.2010.04.006

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  27 in total

1.  PUROMYCIN INHIBITION OF PROTEIN SYNTHESIS: INCORPORATION OF PUROMYCIN INTO PEPTIDE CHAINS.

Authors:  D NATHANS
Journal:  Proc Natl Acad Sci U S A       Date:  1964-04       Impact factor: 11.205

2.  Achromycin: a new antibiotic having trypanocidal properties.

Authors:  J N PORTER; R I HEWITT; C W HESSELTINE; G KRUPKA; J A LOWERY; W S WALLACE; N BOHONOS; J H WILLIAMS
Journal:  Antibiot Chemother (Northfield)       Date:  1952-08

3.  Synthesis of cyclohexyl carbocyclic puromycin and its inhibition of protein synthesis.

Authors:  R Vince; S Daluge
Journal:  J Med Chem       Date:  1977-07       Impact factor: 7.446

4.  Substrate-dependent dihydroxylation of substituted cyclopentenes: toward the syntheses of carbocyclic sinefungin and noraristeromycin.

Authors:  May Xiao-Wu Jiang; Bohan Jin; Jennifer L Gage; Alain Priour; Gordon Savela; Marvin J Miller
Journal:  J Org Chem       Date:  2006-05-26       Impact factor: 4.354

5.  Application of phosphoramidate ProTide technology significantly improves antiviral potency of carbocyclic adenosine derivatives.

Authors:  Christopher McGuigan; Alshaimaa Hassan-Abdallah; Sheila Srinivasan; Yikang Wang; Adam Siddiqui; Susan M Daluge; Kristjan S Gudmundsson; Huiqiang Zhou; Ed W McLean; Jennifer P Peckham; Thimysta C Burnette; Harry Marr; Richard Hazen; Lynn D Condreay; Lance Johnson; Jan Balzarini
Journal:  J Med Chem       Date:  2006-11-30       Impact factor: 7.446

6.  Synthesis and biological evaluation of purealin and analogues as cytoplasmic dynein heavy chain inhibitors.

Authors:  Guangyu Zhu; Fanglong Yang; Raghavan Balachandran; Peter Höök; Richard B Vallee; Dennis P Curran; Billy W Day
Journal:  J Med Chem       Date:  2006-03-23       Impact factor: 7.446

7.  Synthesis and anti-HIV activity of carbocyclic 2',3'-didehydro-2',3'-dideoxy 2,6-disubstituted purine nucleosides.

Authors:  R Vince; M Hua
Journal:  J Med Chem       Date:  1990-01       Impact factor: 7.446

8.  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

9.  N-sulfonyloxy carbamates as reoxidants for the tethered aminohydroxylation reaction.

Authors:  Timothy J Donohoe; Majid J Chughtai; David J Klauber; David Griffin; Andrew D Campbell
Journal:  J Am Chem Soc       Date:  2006-03-01       Impact factor: 15.419

10.  Effect of puromycin analogues and other agents on peptidyl-puromycin synthesis on polyribosomes.

Authors:  S Pestka; R Vince; S Daluge; R Harris
Journal:  Antimicrob Agents Chemother       Date:  1973-07       Impact factor: 5.191
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  3 in total

1.  Palladium(0)/indium iodide-mediated allylations of electrophiles generated from the hydrolysis of Eschenmoser's salt: One-pot preparation of diverse carbocyclic scaffolds.

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

2.  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

Review 3.  Application of asymmetric Sharpless aminohydroxylation in total synthesis of natural products and some synthetic complex bio-active molecules.

Authors:  Majid M Heravi; Tahmineh Baie Lashaki; Bahareh Fattahi; Vahideh Zadsirjan
Journal:  RSC Adv       Date:  2018-02-09       Impact factor: 4.036
  3 in total

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