Inoue H, May E L
J Med Chem. 1976 Feb;19(2):259-62. doi: 10.1021/jm00224a012.
2,9alpha-Dimethyl-2'-hydroxy-6,7-benzomorphan (14) has been synthesized in six to seven steps from trans-3,4-dihydro-4-(2-dimethylaminoethyl)-6-methoxy-3-methyl-1(2H)-naphthalenone (1). The key reaction of the sequence was mercuric acetate cyclization of trans-1,2-dihydro-1-(2-methylaminoethyl)-7-methoxy-2-methylnaphthalene (8) which gave a mixture of 9alpha-methyl-8alpha-hydroxy-6,7-benzomorphan (9, 49%), the corresponding acetate (10, 13%), and the 9beta-methyl-8alpha-hydroxy-6,7-benzomorphan (11, 5%). In the presence of Et3N, the yields were 16, 37, and 0%, respectively. Structural assignments are based on ir, NMR, and mass spectral data and on chemical conversions.
2,9α-二甲基-2'-羟基-6,7-苯并吗啡烷（14）已由反式-3,4-二氢-4-(2-二甲基氨基乙基)-6-甲氧基-3-甲基-1(2H)-萘酮（1）经六至七步合成。该反应序列的关键反应是反式-1,2-二氢-1-(2-甲基氨基乙基)-7-甲氧基-2-甲基萘（8）的醋酸汞环化反应，该反应得到9α-甲基-8α-羟基-6,7-苯并吗啡烷（9，49%）、相应的醋酸酯（10，13%）和9β-甲基-8α-羟基-6,7-苯并吗啡烷（11，5%）的混合物。在三乙胺存在下，产率分别为16%、37%和0%。结构归属基于红外光谱、核磁共振光谱和质谱数据以及化学转化。
