Literature DB >> 16841092

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

Wayne W Harding, Matthis Hodge, Zhixia Wang, William L Woolverton, Damon Parrish, Jeffrey R Deschamps, Thomas E Prisinzano.   

Abstract

The enantioselective synthesis of the (R,R)- and (S,S)-enantiomers of 1 from commercially available 3-chlorocinnamic acid is reported. The Sharpless asymmetric epoxidation was used to establish the stereocenters in the synthesis of both enantiomers of 1.

Entities:  

Year:  2005        PMID： 16841092      PMCID： PMC1502147          DOI： 10.1016/j.tetasy.2005.06.012

Source DB:  PubMed          Journal:  Tetrahedron Asymmetry        ISSN： 0957-4166


  23 in total

1.  Unexpected catalyst for Wittig-type and dehalogenation reactions.

Authors:  Zheng-Zheng Huang; Yong Tang
Journal:  J Org Chem       Date:  2002-07-26       Impact factor: 4.354

2.  The discriminative stimulus effects of cocaine in pigeons.

Authors:  C E Johanson; J E Barrett
Journal:  J Pharmacol Exp Ther       Date:  1993-10       Impact factor: 4.030

3.  [3H]nisoxetine: a radioligand for quantitation of norepinephrine uptake sites by autoradiography or by homogenate binding.

Authors:  S M Tejani-Butt
Journal:  J Pharmacol Exp Ther       Date:  1992-01       Impact factor: 4.030

Review 4.  Monoamine transporters: from genes to behavior.

Authors:  Raul R Gainetdinov; Marc G Caron
Journal:  Annu Rev Pharmacol Toxicol       Date:  2002-09-17       Impact factor: 13.820

5.  Chiral synthesis of (2S,3S)-2-(2-morpholin-2-yl-2-phenylmethoxy)phenol.

Authors:  Jaya Prabhakaran; Vattoly J Majo; J John Mann; J S Dileep Kumar
Journal:  Chirality       Date:  2004-03       Impact factor: 2.437

6.  Efficient, stereoselective synthesis of trans-2,5-disubstituted morpholines.

Authors:  Brian A Lanman; Andrew G Myers
Journal:  Org Lett       Date:  2004-03-18       Impact factor: 6.005

Review 7.  Studying the neurobiology of stimulant and alcohol abuse and dependence in genetically manipulated mice.

Authors:  D N Stephens; A N Mead; T L Ripley
Journal:  Behav Pharmacol       Date:  2002-09       Impact factor: 2.293

Review 8.  Monoamine transporters and psychostimulant drugs.

Authors:  Richard B Rothman; Michael H Baumann
Journal:  Eur J Pharmacol       Date:  2003-10-31       Impact factor: 4.432

9.  A novel and facile preparation of bremazocine enantiomers through optically pure N-norbremazocines.

Authors:  Elisabeth Greiner; John E Folk; Arthur E Jacobson; Kenner C Rice
Journal:  Bioorg Med Chem       Date:  2004-01-02       Impact factor: 3.641

10.  Syntheses and binding studies of new [(aryl)(aryloxy)methyl]piperidine derivatives and related compounds as potential antidepressant drugs with high affinity for serotonin (5-HT) and norepinephrine (NE) transporters.

Authors:  Aurelio Orjales; Ramón Mosquera; Antonio Toledo; M Carmen Pumar; Neftalí García; Lourdes Cortizo; Luis Labeaga; Ana Innerárity
Journal:  J Med Chem       Date:  2003-12-04       Impact factor: 7.446
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  1 in total

1.  Synthesis and biological evaluation of novel 1-alkyl-tryptophan analogs as potential antitumor agents.

Authors:  Ting Sun; Zhao-Long Li; Hua Tian; Shih-Chen Wang; Jiong Cai
Journal:  Molecules       Date:  2009-12-18       Impact factor: 4.411
  1 in total

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