Synthesis of morphine fragments spiro[benzofuran-3(2H),4′-piperidine] and octahydro-1H-benzofuro[3,2-e]isoquinoline by intramolecular Heck reaction
作者:Chen-Yu Cheng、Jing-Ping Liou、Mei-Jing Lee
DOI:10.1016/s0040-4039(97)00976-3
日期:1997.6
As a better alternative to radical cyclization, 5-(2-bromo-6-methoxyphenoxy)-2-methyl-1,2,3,4,5,6,7,8-octahydroisoquinoline (2) and its 1-oxo analog 3 underwent Pd-catalyzed intramolecular cyclization to give the tetracyclic (ACNO) morphine fragments 5 and 6 respectively. 4-[(2′-Iodo-6′-methoxyphenoxy)methyl]-1-ethoxycarbonyl-1,2,5,6,-tetrahydropyridine (11) reacted similarly to provide the tricyclic
作为自由基环化的更好替代方法,5-(2-溴-6-甲氧基苯氧基)-2-甲基-1,2,3,4,5,6,7,8-八氢异喹啉(2)及其1-氧代类似物3进行Pd催化的分子内环化,分别得到四环(ACNO)吗啡片段5和6。4-[(2'-碘-6'-甲氧基苯氧基)甲基] -1-乙氧基羰基-1,2,5,6,-四氢吡啶(11)类似地反应以70%的收率和45%的产率提供三环ANO片段12当使用Pd-(S)-BINAP配合物作为催化剂时。