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Literature DB >> 28579652

Enantioselective Synthesis of α-Bromonitroalkanes for Umpolung Amide Synthesis: Preparation of tert-Butyl ((1R)-1-(4-(benzyloxy)phenyl)-2-bromo-2-nitroethyl)carbamate.

Victoria T Lim¹, Sergey V Tsukanov¹, Amanda B Stephens¹, Jeffrey N Johnston¹.

Abstract

Entities: Chemical Disease Gene Species

Mesh：

Substances：
Amides
Carbamates

Year: 2016 PMID： 28579652 PMCID： PMC5453646 DOI： 10.15227/orgsyn.093.0088

Source DB: PubMed Journal: Organic Synth ISSN： 0078-6209

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11 in total

Review 1. Developments in peptide and amide synthesis.

Authors: Fernando Albericio
Journal: Curr Opin Chem Biol Date: 2004-06 Impact factor: 8.822

2. The antiviral antibiotic feglymycin: first direct-methods solution of a 1000+ equal-atom structure.

Authors: Gábor Bunkóczi; László Vértesy; George M Sheldrick
Journal: Angew Chem Int Ed Engl Date: 2005-02-18 Impact factor: 15.336

3. Total synthesis of the antiviral peptide antibiotic feglymycin.

Authors: Frank Dettner; Anne Hänchen; Dominique Schols; Luigi Toti; Antje Nusser; Roderich D Süssmuth
Journal: Angew Chem Int Ed Engl Date: 2009 Impact factor: 15.336

4. Feglymycin, a novel inhibitor of the replication of the human immunodeficiency virus. Fermentation, isolation and structure elucidation.

Authors: L Vértesy; W Aretz; M Knauf; A Markus; M Vogel; J Wink
Journal: J Antibiot (Tokyo) Date: 1999-04 Impact factor: 2.649

5. Discovery of competing anaerobic and aerobic pathways in umpolung amide synthesis allows for site-selective amide 18O-labeling.

Authors: Jessica P Shackleford; Bo Shen; Jeffrey N Johnston
Journal: Proc Natl Acad Sci U S A Date: 2011-12-19 Impact factor: 11.205

Review 6. Rethinking amide bond synthesis.

Authors: Vijaya R Pattabiraman; Jeffrey W Bode
Journal: Nature Date: 2011-12-21 Impact factor: 49.962

Enantioselective Synthesis of α-Bromonitroalkanes for Umpolung Amide Synthesis: Preparation of tert-Butyl ((1R)-1-(4-(benzyloxy)phenyl)-2-bromo-2-nitroethyl)carbamate.

Review 1. Developments in peptide and amide synthesis.

2. The antiviral antibiotic feglymycin: first direct-methods solution of a 1000+ equal-atom structure.

3. Total synthesis of the antiviral peptide antibiotic feglymycin.

4. Feglymycin, a novel inhibitor of the replication of the human immunodeficiency virus. Fermentation, isolation and structure elucidation.

5. Discovery of competing anaerobic and aerobic pathways in umpolung amide synthesis allows for site-selective amide 18O-labeling.

Review 6. Rethinking amide bond synthesis.

7. Umpolung reactivity in amide and peptide synthesis.

8. N-heterocyclic carbene (NHC)-catalyzed direct amidation of aldehydes with nitroso compounds.

9. Preparation of H,(4) PyrrolidineQuin-BAM (PBAM).

Review 10. Amide bond formation: beyond the myth of coupling reagents.

1. Resolving Bromonitromethane Sourcing by Synthesis: Preparation at the Decagram Scale.

2. Fluorine-induced diastereodivergence discovered in an equally rare enantioselective syn-aza-Henry reaction.