Literature DB >> 20607121

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

Cheng Ji1, Marvin J Miller.   

Abstract

Treatment of nitroso Diels-Alder cycloadducts 1 with diazomethane in the presence of palladium acetate gives synthetically useful exo-6-oxa-7-azatricyclo[3.2.1.02,4]octane derivatives 7 in good to excellent yield. Using this methodology, a conformationally restricted 2',3'-methano carbocyclic nucleoside was efficiently synthesized from nitroso cycloadduct 1a in 7 steps.

Entities:  

Year:  2010        PMID： 20607121      PMCID： PMC2894734          DOI： 10.1016/j.tetlet.2010.05.062

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


  30 in total

1.  The synthesis and in vitro testing of structurally novel antibiotics derived from acylnitroso Diels-Alder adducts.

Authors:  George P Nora; Marvin J Miller; Ute Möllmann
Journal:  Bioorg Med Chem Lett       Date:  2006-05-26       Impact factor: 2.823

2.  Stereoselective synthesis of conformationally rigid apio carbanucleosides as potential antiviral agents.

Authors:  Hyung Ryong Moon; Kyung Ran Kim; Bum Tae Kim; Ki Jun Hwang; Moon Woo Chun; Lak Shin Jeong
Journal:  Nucleosides Nucleotides Nucleic Acids       Date:  2005       Impact factor: 1.381

3.  Regio- and stereochemically controlled formation of hydroxamic acid containing anti- or syn-1,4-cycloalkenols from acylnitroso-derived Diels-Alder adducts.

Authors:  M D Surman; M J Miller
Journal:  J Org Chem       Date:  2001-04-06       Impact factor: 4.354

4.  Brønsted acid-mediated opening of nitroso cycloadducts under anhydrous conditions.

Authors:  Brian S Bodnar; Marvin J Miller
Journal:  Tetrahedron Lett       Date:  2009-02-18       Impact factor: 2.415

5.  Syntheses of new spirocarbocyclic nucleoside analogs using iminonitroso Diels-Alder reactions.

Authors:  Weimin Lin; Anuradha Gupta; Kyung Hee Kim; David Mendel; Marvin J Miller
Journal:  Org Lett       Date:  2009-01-15       Impact factor: 6.005

6.  Stereoselective cycloadditions of chiral acyl-nitroso compounds; selective reactions of ring-cleaved cycloadducts leading to a new approach to polyoxamic acid.

Authors:  Adrian G Pepper; Garry Procter; Martyn Voyle
Journal:  Chem Commun (Camb)       Date:  2002-05-21       Impact factor: 6.222

Review 7.  Recent advances in the synthesis of conformationally locked nucleosides and their success in probing the critical question of conformational preferences by their biological targets.

Authors:  Yongseok Choi; Hyung R Moon; Yuichi Yoshimura; Victor E Marquez
Journal:  Nucleosides Nucleotides Nucleic Acids       Date:  2003 May-Aug       Impact factor: 1.381

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.  Synthesis and conformational analysis of a locked analogue of carbovir built on a bicyclo[3.1.0]hex-2-enyl template.

Authors:  Yongseok Choi; Guangyu Sun; Clifford George; Marc C Nicklaus; James A Kelley; Victor E Marquez
Journal:  Nucleosides Nucleotides Nucleic Acids       Date:  2003-12       Impact factor: 1.381

10.  Synthesis of conformationally locked carbocyclic nucleoside phosphonates to probe the active site of HIV-1 RT.

Authors:  Hisao Saneyoshi; B Christie Vu; Stephen H Hughes; Paul L Boyer; Stefan G Sarafianos; Victor E Marquez
Journal:  Nucleic Acids Symp Ser (Oxf)       Date:  2008
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  3 in total

1.  Continuous flow of nitroso Diels-Alder reaction.

Authors:  Erika Nakashima; Hisashi Yamamoto
Journal:  Chem Commun (Camb)       Date:  2015-08-07       Impact factor: 6.222

2.  Syntheses and biological studies of novel spiropiperazinyl oxazolidinone antibacterial agents using a spirocyclic diene derived acylnitroso Diels-Alder reaction.

Authors:  Cheng Ji; Weimin Lin; Garrett C Moraski; Jane A Thanassi; Michael J Pucci; Scott G Franzblau; Ute Möllmann; Marvin J Miller
Journal:  Bioorg Med Chem       Date:  2012-04-18       Impact factor: 3.641

3.  Acid-catalyzed ring-opening reactions of a cyclopropanated 3-aza-2-oxabicyclo[2.2.1]hept-5-ene with alcohols.

Authors:  Katrina Tait; Alysia Horvath; Nicolas Blanchard; William Tam
Journal:  Beilstein J Org Chem       Date:  2017-12-27       Impact factor: 2.883
  3 in total

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