Synthesis of enantiopure 10-nornaltrexones in the search for Toll-like receptor 4 antagonists and opioid ligands

…, JR Deschamps, AE Jacobson, KC Rice

Index: Selfridge, Brandon R.; Deschamps, Jeffrey R.; Jacobson, Arthur E.; Rice, Kenner C. Journal of Organic Chemistry, 2014 , vol. 79, # 11 p. 5007 - 5018

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Citation Number: 2

Abstract

10-Nornaltrexones (3-(cyclopropylmethyl)-4a, 9-dihydroxy-2, 3, 4, 4a, 5, 6-hexahydro-1 H- benzofuro [3, 2-e] isoquinolin-7 (7a H)-one, 1) have been underexploited in the search for better opioid ligands, and their enantiomers have been unexplored. The synthesis of trans- isoquinolinone 2 (4-aH, 9-O-trans-9-methoxy-3-methyl-2, 3, 4, 4a, 5, 6-hexahydro-1 H- benzofuro [3, 2-e] isoquinolin-7 (7a H)-one) was achieved through a nonchromatographic ...