R,R-(-)-蝙蝠葛苏林碱的全合成

TOTAL SYNTHESIS OF R,R-(-)-DAURISOLINE

摘要: 本文报道以香兰素和苯乙腈为起始原料。通过硝化、还原、缩合,毕歇尔纳皮尔斯基反应和拆分,分别制得关键中间体R-(—)-1-(3′-溴-苄氧基)苄基-2-甲基-6-甲氧基-7-苄氧基-1,2,3,4-四氢异喹啉(3)和R-(—)-1-(4′-羟基)苄基-2-甲基-6,7-二甲氧基-1,2,3,4,-四氢异喹啉(4)。(3)和(4)再经乌尔门反应及盐酸-乙醇去苄基合成R,R-(—)-蝙蝠葛苏林碱(1),并确证了(1)的结构与天然蝙蝠葛苏林碱一致。

Abstract: Daurisoline(1) was identified as a bisbenzyltetrahydroisoquinoline alkaloid bearing one ether linkage. The key intermediates R-(-)-l-(3'-bromo-4' -benzyloxy)benzyl-1-2-methyl-6-methoxy-7-benzyloxy -1,2,3,4-tetrahydroisoquinoline(3) and R-(-)-l-(4'-hydroxy