Fachbereich Chemie, Philipps-University Marburg, Hans-Meerwein-Strasse, D-35032 Marburg, Germany.
Org Lett. 2010 Sep 3;12(17):3808-11. doi: 10.1021/ol101500k.
The synthesis of the pyrrolopyrrole substructure of the isoquinocyclines is reported. The pentacyclic (CDEFG) substructure of isoquinocycline A and B, which contains an unusual 2,4,5,6-tetrahydropyrrolo[2,3-b]pyrrole (FG) connected via an N,O-spiro acetal to the anthraquinoid core of the isoquinocycline aglycon has been synthesized. Key steps were a nickel(0)-mediated hydrocyanation of an alkynone, the conversion of an O,O-acetal into an N,O-acetal, and an intramolecular amidine alkylation.
报告了异喹诺环素中吡咯并吡咯亚结构的合成。含有通过 N,O-螺缩醛与异喹诺环素糖苷元的蒽醌核心连接的不寻常的 2,4,5,6-四氢吡咯并[2,3-b]吡咯 (FG) 的五环 (CDEFG) 亚结构已经被合成。关键步骤包括镍(0)介导的炔酮的氢氰化反应、O,O-缩醛转化为 N,O-缩醛以及分子内脒烷基化反应。
