Asymmetric Synthesis Of Spiro Oxindole Alkaloids Horsfiline And Coerulescine

The spiro oxindole alkaloids horsfiline and coerulescine have received extensive attention from the chemical community since they were isolated.A striking structural feature of the tricyclic oxindole alkaloids is the presence of a quaternary carbon(the spiro center C-3)with a pyrrolidine substitution.The construction of the chiral quaternary carbon center is also the focus of the synthesis of this type of compound.In this paper,a large number of Tsuji-Trost reaction conditions were screened,and the reaction conditions for the construction of a key chiral quaternary carbon center with the separation yield of 50% and 90% ee were obtained.It can complete the total synthesis of natural products horsfiline and coerulescine.This article is divided into three chapters.The first chapter is divided into two subsections.The first subsection introduces the synthetic research progress of natural products horsfiline and coerulescine,and the second subsection introduces the asymmetric allylic alkylation.The second chapter consists of two parts.The first part studies the total synthesis of spirocyclic oxindole natural products horsfiline and coerulescine.The second part conducts a methodological study of the Tsuji-Trost reaction conditions we developed.The third chapter mainly introduces the specific operation of the experiment,the HPLC of chiral compounds and the NMR data of the main compounds.