… ., 6a. alpha., 11a. beta.)-1, 3, 4, 5, 6, 11a-hexahydro-2-methyl-2H-3, 6a-methanobenzofuro [2, 3-c] azocin-10-ol, and oxide-bridged 5-(m-hydroxyphenyl) morphan

…, BA Weissman, HC Huang, JV Silverton

Index: Burke, Terrence R.; Jacobson, Arthur E.; Rice, Kenner C.; Weissman, Ben Avi; Huang, Hsueh-Cheng; Silverton, J. V. Journal of Medicinal Chemistry, 1986 , vol. 29, # 5 p. 748 - 751

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Citation Number: 24

Abstract

The synthesis of racemic (31~, 6a~~, 11~)-1, 3, 4, 5, 6, 11a-hexahydro-2-methy1-~-3, 6a- methanobe~ ofuro [2, 3-c] azocin-10-o1 (2d) is described. The route used acid-catalyzed ring closure of enamine 5 to yield the unsaturated phenylmorphan 6. Conversion of 6 to oxide-bridged 2d was accomplished in a multistep fashion that utilized the introduction of a bromine atom, followed by 0-demethylation of the phenolic methyl ethers and base- ...