O'Connor Patrick D, Mander Lewis N, McLachlan Matthew M W
Research School of Chemistry, Australian National University, Canberra, ACT 0200, Australia.
Org Lett. 2004 Mar 4;6(5):703-6. doi: 10.1021/ol036308n.
The hexacyclic himandrine skeleton 5, which is present in the most complex alkaloids of the tropical rain forest tree Galbulimima belgraveana, has been prepared for the first time. The synthesis begins from the known [3.2.1]benzobicyclooctene intermediate 10. Key steps include a Diels-Alder cycloaddition, Curtius rearrangement, Birch reduction, an intramolecular nucleophilic amination, and a palladium-mediated alkene amination. [reaction: see text]
已首次制备出六环海芒果骨架5，其存在于热带雨林树木加布梨木（Galbulimima belgraveana）最复杂的生物碱中。该合成从已知的[3.2.1]苯并双环辛烯中间体10开始。关键步骤包括狄尔斯-阿尔德环加成反应、库尔提斯重排反应、伯奇还原反应、分子内亲核胺化反应以及钯介导的烯烃胺化反应。[反应：见正文]
