36193-36-9Relevant articles and documents
Catalytically Asymmetric Pd/Norbornene Catalysis: Enantioselective Synthesis of (+)-Rhazinal, (+)-Rhazinilam, and (+)-Kopsiyunnanine C1-3
Zhao, Kun,Xu, Shibo,Pan, Chongqing,Sui, Xianwei,Gu, Zhenhua
supporting information, p. 3782 - 3785 (2016/08/16)
A catalytically asymmetric palladium/norbornene-catalyzed reaction is reported, where α-aryl tetrahydroquinoline derived phosphoramidite L15 is found to be the optimum ligand. Taking advantage of this transformation, the concise and unified enantioselective syntheses of (+)-rhazinal, (+)-rhazinilam, and (+)-kopsiyunnanine C1, C2, and C3 are realized.
Solvent-controlled switchable C-H alkenylation of 4-aryl-1H-pyrrole-3-carboxylates: Application to the total synthesis of (±)-rhazinilam
Su, Youla,Zhou, Haipin,Chen, Jiaxuan,Xu, Jinyi,Wu, Xiaoming,Lin, Aijun,Yao, Hequan
, p. 4884 - 4887 (2015/04/27)
A solvent-controlled switchable C-H alkenylation of 4-aryl-1H-pyrrole-3-carboxylates via a Pd(OAc)2 catalyzed oxidative Heck reaction was first realized. The corresponding C2 and C5 alkenylation products were obtained in good yields with high regioselectivities, respectively. The selective C5-alkenylation was successfully applied to the total synthesis of (±)-rhazinilam.
Chemical synthesis of aspidosperma alkaloids inspired by the reverse of the biosynthesis of the rhazinilam family of natural products
McMurray, Lindsay,Beck, Elizabeth M.,Gaunt, Matthew J.
, p. 9288 - 9291 (2012/10/30)
Pyrrole reduction: Iterative metal-catalyzed C-H functionalization reactions facilitated the preparation of a highly substituted pyrrole derivative. This derivative could be transformed into the pyrrole-containing secondary metabolite, rhazinilam, which could in turn be transformed through a reductive transannular cascade process into the structurally complex pyrrolidine-containing alkaloid natural product, aspidospermidine.