Literature DB >> 21905747

Diastereoselective one-pot synthesis of 7- and 8-substituted 5-phenylmorphans.

Hwan Jung Lim1, Jeffrey R Deschamps, Arthur E Jacobson, Kenner C Rice.   

Abstract

Novel 7- and 8-alkyl and aryl substituted 5-phenylmorphans were synthesized from substituted allyl halides and N-benzyl-4-aryl-1,2,3,6-tetrahydropyridine by a highly efficient and diastereoselective reaction series, "one-pot" alkylation and ene-imine cyclization followed by sodium borohydride reduction. Mild cyclization conditions gave the desired substituted 5-phenylmorphans in good yield as a single diastereomer.
© 2011 American Chemical Society

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Year:  2011        PMID： 21905747      PMCID： PMC3351792          DOI： 10.1021/ol2021862

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


  6 in total

1.  Improved synthesis and additional pharmacology of the potent analgetic (-)-5-m-hydroxyphenyl-2-methylmorphan.

Authors:  M E Rogers; E L May
Journal:  J Med Chem       Date:  1974-12       Impact factor: 7.446

2.  Opioid ligands with mixed properties from substituted enantiomeric N-phenethyl-5-phenylmorphans. Synthesis of a micro-agonist delta-antagonist and delta-inverse agonists.

Authors:  Kejun Cheng; In Jong Kim; Mei-Jing Lee; Steven A Adah; Tyler J Raymond; Edward J Bilsky; Mario D Aceto; Everette L May; Louis S Harris; Andrew Coop; Christina M Dersch; Richard B Rothman; Arthur E Jacobson; Kenner C Rice
Journal:  Org Biomol Chem       Date:  2007-03-01       Impact factor: 3.876

3.  Probes for narcotic receptor mediated phenomena. 9. Synthesis of (+/-)-(3 alpha,6a alpha,11a beta)-1,3,4,5,6,11a-hexahydro-2-methyl-2H-3,6a- methanobenzofuro[2,3-c]azocin-10-ol, an oxide-bridged 5-(m-hydroxyphenyl)morphan.

Authors:  T R Burke; A E Jacobson; K C Rice; B A Weissman; H C Huang; J V Silverton
Journal:  J Med Chem       Date:  1986-05       Impact factor: 7.446

4.  Discovery of an opioid kappa receptor selective pure antagonist from a library of N-substituted 4beta-methyl-5-(3-hydroxyphenyl)morphans.

Authors:  James B Thomas; Robert N Atkinson; Nivedita Namdev; Richard B Rothman; Kenneth M Gigstad; Scott E Fix; S Wayne Mascarella; Jason P Burgess; N Ariane Vinson; Heng Xu; Christina M Dersch; Buddy E Cantrell; Dennis M Zimmerman; F Ivy Carroll
Journal:  J Med Chem       Date:  2002-08-01       Impact factor: 7.446

5.  Probes for narcotic receptor-mediated phenomena. 20. Alteration of opioid receptor subtype selectivity of the 5-(3-hydroxyphenyl)morphans by application of the message-address concept: preparation of delta-opioid receptor ligands.

Authors:  C M Bertha; J L Flippen-Anderson; R B Rothman; F Porreca; P Davis; H Xu; K Becketts; X Y Cha; K C Rice
Journal:  J Med Chem       Date:  1995-04-28       Impact factor: 7.446

6.  Probes for narcotic receptor mediated phenomena. 34. Synthesis and structure-activity relationships of a potent mu-agonist delta-antagonist and an exceedingly potent antinociceptive in the enantiomeric C9-substituted 5-(3-hydroxyphenyl)-N-phenylethylmorphan series.

Authors:  Anne-Cécile Hiebel; Yong Sok Lee; Edward Bilsky; Denise Giuvelis; Jeffrey R Deschamps; Damon A Parrish; Mario D Aceto; Everette L May; Louis S Harris; Andrew Coop; Christina M Dersch; John S Partilla; Richard B Rothman; Kejun Cheng; Arthur E Jacobson; Kenner C Rice
Journal:  J Med Chem       Date:  2007-07-11       Impact factor: 7.446
  6 in total
  2 in total

1.  Probes for narcotic receptor mediated phenomena. 46. N-substituted-2,3,4,9,10,10a-hexahydro-1H-1,4a-(epiminoethano)phenanthren-6- and 8-ols - carbocyclic relatives of f-oxide-bridged phenylmorphans.

Authors:  Fuying Li; Jason A Deck; Christina M Dersch; Richard B Rothman; Jeffrey R Deschamps; Arthur E Jacobson; Kenner C Rice
Journal:  Eur J Med Chem       Date:  2012-10-30       Impact factor: 6.514

2.  Probes for narcotic receptor mediated phenomena. 48. C7- and C8-substituted 5-phenylmorphan opioids from diastereoselective alkylation.

Authors:  Hwan Jung Lim; Christina M Dersch; Richard B Rothman; Jeffrey R Deschamps; Arthur E Jacobson; Kenner C Rice
Journal:  Eur J Med Chem       Date:  2013-06-25       Impact factor: 6.514
  2 in total

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