Probes for narcotic receptor mediated phenomena. 4. Synthesis of (.+-.)-2, 3, 4, 5, 6, 6a-hexahydro-3-methyl-8-hydroxy-1H-4, 11b-methanobenzofuro [3, 2-d] azocine, …

…, AE Jacobson, KC Rice, JV Silverton

Index: Burke Jr.; Jacobson; Rice; Silverton Journal of Organic Chemistry, 1984 , vol. 49, # 6 p. 1051 - 1056

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Citation Number: 23

Abstract

The synthesis of racemic 2, 3, 4, 5, 6, 6a-hexahydro-3-methyl-3-hydroxy-1H-4, 1lb- methanobenzofuro [3, 2-d] azocine (2) is described. The route utilized a key photochemical conversion of the aryloxy enone 7 to the hexahydrodibenzofuran 8, which established the relative stereochemistry of the oxide and methano bridges of 2. A 1, 4-Michael-type addition of nitrogen to the@-carbon of the a,@-unsaturated compound 12 establishedthe fourth ...