Department of Medicinal Chemistry, University of Kansas, 1251 Wescoe Hall Drive, Lawrence, Kansas 66045, USA.
Org Lett. 2011 Jan 21;13(2):196-9. doi: 10.1021/ol1023954. Epub 2010 Dec 14.
A highly convergent strategy to prepare phenanthroindolizidines is reported involving three consecutive C-C coupling reactions. This sequence features a novel VOF(3)-mediated aryl-alkene coupling in the final step, which enables regioselective preparation of C5-substituted phenanthroindolizidines for the first time. This strategy has been applied to the synthesis of eight natural and unnatural members in this class to investigate the scope of this chemistry and to explore structure-activity relationships.
本文报道了一种高度汇聚的策略来制备菲并吲哚里嗪，涉及三个连续的 C-C 偶联反应。该序列的最后一步具有新颖的 VOF(3)介导的芳基-烯烃偶联，这使得首次能够区域选择性地制备 C5 取代的菲并吲哚里嗪。该策略已应用于该类化合物的八个天然和非天然成员的合成，以研究该化学的范围并探索结构-活性关系。
