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Synthesis of rac-(1R,4aR,9aR)-2-methyl-1,3,4,9a-tetrahydro-2H-1,4a-propanobenzofuro[2,3-c]pyridin-6-ol. An unusual double rearrangement leading to the ortho- and para-f oxide-bridged phenylmorphan isomers.
Kodato S, Linders JT, Gu XH, Yamada K, Flippen-Anderson JL, Deschamps JR, Jacobson AE, Rice KC. Kodato S, et al. Among authors: deschamps jr. Org Biomol Chem. 2004 Feb 7;2(3):330-6. doi: 10.1039/b312633c. Epub 2004 Jan 5. Org Biomol Chem. 2004. PMID: 14747861
Probes for narcotic receptor-mediated phenomena. 33. Construction of a strained trans-5,6-ring system by displacement of a nitro-activated aromatic fluorine. synthesis of the penultimate oxide-bridged phenylmorphans.
Hashimoto A, Przybyl AK, Linders JT, Kodato S, Tian X, Deschamps JR, George C, Flippen-Anderson JL, Jacobson AE, Rice KC. Hashimoto A, et al. Among authors: deschamps jr. J Org Chem. 2004 Aug 6;69(16):5322-7. doi: 10.1021/jo040159k. J Org Chem. 2004. PMID: 15287777
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.
Hiebel AC, Lee YS, Bilsky E, Giuvelis D, Deschamps JR, Parrish DA, Aceto MD, May EL, Harris LS, Coop A, Dersch CM, Partilla JS, Rothman RB, Cheng K, Jacobson AE, Rice KC. Hiebel AC, et al. Among authors: deschamps jr. J Med Chem. 2007 Aug 9;50(16):3765-76. doi: 10.1021/jm061325e. Epub 2007 Jul 11. J Med Chem. 2007. PMID: 17625813
Probes for narcotic receptor mediated phenomena. 37. Synthesis and opioid binding affinity of the final pair of oxide-bridged phenylmorphans, the ortho- and para-b-isomers and their N-phenethyl analogues, and the synthesis of the N-phenethyl analogues of the ortho- and para-d-isomers.
Kurimura M, Liu H, Sulima A, Hashimoto A, Przybyl AK, Ohshima E, Kodato S, Deschamps JR, Dersch CM, Rothman RB, Lee YS, Jacobson AE, Rice KC. Kurimura M, et al. Among authors: deschamps jr. J Med Chem. 2008 Dec 25;51(24):7866-81. doi: 10.1021/jm800913d. J Med Chem. 2008. PMID: 19053757 Free PMC article.
206 results