A formal synthesis of aspidospermidine is reported through a novel preparation of Stork's penultimate tricyclic ketone intermediate. The key steps of the synthesis consist of an intramolecular cascade transannular cyclization, triggered by the removal of Boc group, which simultaneously forms the C, D, and E rings of aspidospermidine and conveniently setting up the quaternary stereo-center via decarboxylative alkylation reaction of the beta-keto ester.
1.Chinese Acad Sci, State Key Lab Phytochem & Plant Resources West Ch, Kunming Inst Bot, Kunming 650201, Peoples R China 2.Yunnan Univ, Key Lab Med Chem Nat Resource, Kunming 650091, Peoples R China 3.Zhengzhou Univ, Dept Chem, Zhengzhou 450052, Peoples R China
Recommended Citation:
Huang, Jiu-Zhong; Jie, Xiao-Ke; Wei, Kun; Zhang, Hongbin; Wang, Min-Cai; Yang, Yu-Rong.Formal Synthesis of Aspidospermidine via the Intramolecular Cascade Transannular Cyclization,SYNLETT,2013,(10):1303-1306
