Literature DB >> 19601571

Diastereoselective synthesis of a spironoraristeromycin using an acylnitroso Diels-Alder reaction.

Weimin Lin1, Kristopher G Virga, Kyung-Hee Kim, Jaroslav Zajicek, David Mendel, Marvin J Miller.   

Abstract

The tert-butyl N-hydroxycarbamate-derived nitroso reagent 1 reacted with N-Cbz-protected spirocyclic diene 2 to provide spirocycloadduct 3. Here we describe the efficient conversion of 3 into the novel carbocyclic nucleoside spironoraristeromycin 4.

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Year:  2009        PMID： 19601571      PMCID： PMC2888906          DOI： 10.1021/jo900877b

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


  29 in total

1.  A general and efficient copper catalyst for the amidation of aryl halides and the N-arylation of nitrogen heterocycles.

Authors:  A Klapars; J C Antilla; X Huang; S L Buchwald
Journal:  J Am Chem Soc       Date:  2001-08-08       Impact factor: 15.419

Review 2.  S-adenosyl-L-homocysteine hydrolase as a target for antiviral chemotherapy.

Authors:  M S Wolfe; R T Borchardt
Journal:  J Med Chem       Date:  1991-05       Impact factor: 7.446

Review 3.  Carbocyclic nucleosides.

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

Review 4.  S-adenosylhomocysteine hydrolase inhibitors as broad-spectrum antiviral agents.

Authors:  E De Clercq
Journal:  Biochem Pharmacol       Date:  1987-08-15       Impact factor: 5.858

5.  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

6.  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

Review 7.  Carbocyclic nucleosides (carbanucleosides) as new therapeutic leads.

Authors:  Stewart W Schneller
Journal:  Curr Top Med Chem       Date:  2002-10       Impact factor: 3.295

8.  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

Review 9.  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

10.  Studies on neplanocin A, new antitumor antibiotic. I. Producing organism, isolation and characterization.

Authors:  S Yaginuma; N Muto; M Tsujino; Y Sudate; M Hayashi; M Otani
Journal:  J Antibiot (Tokyo)       Date:  1981-04       Impact factor: 2.649
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  2 in total

1.  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

2.  Davis-Beirut Reaction Inspired Nitroso Diels-Alder Reaction.

Authors:  Jung-Ho Son; Amy Cheung; Jie S Zhu; Makhluf J Haddadin; Mark J Kurth
Journal:  Tetrahedron Lett       Date:  2021-02-23       Impact factor: 2.415
  2 in total

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