Literature DB >> 15727479

Asymmetric synthesis of (+)-(S,S)-reboxetine via a new (S)-2-(hydroxymethyl)morpholine preparation.

Eric Brenner1, Ronald M Baldwin, Gilles Tamagnan.   

Abstract

(S,S)-Reboxetine was synthesized stereospecifically in 30% overall yield and 99% ee in eight steps. Key steps were selective oxidation of an N-protected hydroxymethylmorpholine and aryl-chromium-mediated aromatic nucleophilic substitution. [structure: see text]

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Year:  2005        PMID： 15727479     DOI： 10.1021/ol050059g

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  8 in total

1.  Complexity of Blocking Bivalent Protein-Protein Interactions: Development of a Highly Potent Inhibitor of the Menin-Mixed-Lineage Leukemia Interaction.

Authors:  Dmitry Borkin; Szymon Klossowski; Jonathan Pollock; Hongzhi Miao; Brian M Linhares; Katarzyna Kempinska; Zhuang Jin; Trupta Purohit; Bo Wen; Miao He; Duxin Sun; Tomasz Cierpicki; Jolanta Grembecka
Journal:  J Med Chem       Date:  2018-05-23       Impact factor: 7.446

2.  Fluorine-18 Radiolabeled PET Tracers for Imaging Monoamine Transporters: Dopamine, Serotonin, and Norepinephrine.

Authors:  Jeffrey S Stehouwer; Mark M Goodman
Journal:  PET Clin       Date:  2009-01

3.  Development of SPECT imaging agents for the norepinephrine transporters: [123I]INER.

Authors:  Gilles D Tamagnan; Eric Brenner; David Alagille; Julie K Staley; Colin Haile; Andrei Koren; Michelle Early; Ronald M Baldwin; Frank I Tarazi; Ross J Baldessarini; Nachwa Jarkas; Mark M Goodman; John P Seibyl
Journal:  Bioorg Med Chem Lett       Date:  2006-10-12       Impact factor: 2.823

4.  Enantioselective synthesis of (2R,3R)- and (2S,3S)-2- [(3-chlorophenyl)-(2-methoxyphenoxy)methyl]morpholine.

Authors:  Wayne W Harding; Matthis Hodge; Zhixia Wang; William L Woolverton; Damon Parrish; Jeffrey R Deschamps; Thomas E Prisinzano
Journal:  Tetrahedron Asymmetry       Date:  2005-07-04

5.  Design and synthesis of manganese porphyrins with tailored lipophilicity: investigation of redox properties and superoxide dismutase activity.

Authors:  Dorothée Lahaye; Kannan Muthukumaran; Chen-Hsiung Hung; Dorota Gryko; Júlio S Rebouças; Ivan Spasojević; Ines Batinić-Haberle; Jonathan S Lindsey
Journal:  Bioorg Med Chem       Date:  2007-08-19       Impact factor: 3.641

6.  Synthesis, radiosynthesis, and biological evaluation of carbon-11 and fluorine-18 labeled reboxetine analogues: potential positron emission tomography radioligands for in vivo imaging of the norepinephrine transporter.

Authors:  Fanxing Zeng; Jiyoung Mun; Nachwa Jarkas; Jeffrey S Stehouwer; Ronald J Voll; Gilles D Tamagnan; Leonard Howell; John R Votaw; Clinton D Kilts; Charles B Nemeroff; Mark M Goodman
Journal:  J Med Chem       Date:  2009-01-08       Impact factor: 7.446

7.  Synthesis of enantiomerically pure N-(2,3-dihydroxypropyl)arylamides via oxidative esterification.

Authors:  Akula Raghunadh; Satish S More; T Krishna Chaitanya; Yadla Sateesh Kumar; Suresh Babu Meruva; L Vaikunta Rao; U K Syam Kumar
Journal:  Beilstein J Org Chem       Date:  2013-10-17       Impact factor: 2.883

8.  Efficient Routes to a Diverse Array of Amino Alcohol-Derived Chiral Fragments.

Authors:  Sina Haftchenary; Shawn D Nelson; Laura Furst; Sivaraman Dandapani; Steven J Ferrara; Žarko V Bošković; Samuel Figueroa Lazú; Adrian M Guerrero; Juan C Serrano; DeMarcus K Crews; Cristina Brackeen; Jeffrey Mowat; Thomas Brumby; Marcus Bauser; Stuart L Schreiber; Andrew J Phillips
Journal:  ACS Comb Sci       Date:  2016-08-12       Impact factor: 3.784
  8 in total

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