R,R-(-)-蝙蝠葛苏林碱的全合成

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。

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

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)benzyl-2-methyl-6, 7-dimethoxy-1,2, 3, 4-tetrahydroisoquinoline(4) were obtained from the starting materials, vanillin and benzylcyanid via nitration, reduction, condensation, Bischler-Napieralski reaction and resolution. R,R-(-)-Daurisoling(l) was synthesized by the connection of (3) and (4) via Ullmann reaction and debenzylation with hydrochloric acid and ethanol. The structure study of the synthetic product(l) showed that it was the target compound.