Four 4-phenyl-1, 2, 3, 4-tetrahydroisoquinolines (8b, c, f, g) were prepared from two simple synthons, styrene oxide and the benzylamines (2b-e), via the β-hydroxyphenethylamines (3b-e) in high yield. On the other hand, the β-methoxyphenethyl methanesulfonate (16), obtained from 4-benzyloxystyrene oxide (11), was coupled with the benzylamine (2a) to give the N-benzyl-β-methoxyphenethylamine (17). A facile total synthesis of (±)-cherylline (1) was accomplished by acid treatment of 17.4'-O-Methylcherylline (18) was also synthesized through the same pathway.
四种 4-苯基-1, 2, 3, 4-
四氢异喹啉(8b, c, f, g)是由两种简单的合成物--
氧化苯乙烯和
苄胺(2b-e)通过 β-羟基苯
乙胺(3b-e)以高收率制备的。另一方面,从 4-苄氧基
苯乙烯氧化物(11)得到的 β-
甲氧基苯乙基
甲磺酸盐(16)与
苄胺(2a)偶联得到 N-苄基-β-
甲氧基苯乙胺(17)。通过对 17.4'-O-Methylcherylline (18) 的酸处理,还通过相同的途径合成了 (±)-cherylline (1)。