Studies On The Synthesis And Activity Of Caesalpinnone A

This paper takes the synthesis and activity of Caesalpinnone A as the research object,based on the [4+2] cycloaddition reaction of o-quinone methides(o QMs),introduces the formation of o-quinone methide(o QMs),the research status of this reaction and its application in total synthesis,especially in the synthesis of benzopyran natural products.The synthetic strategy was applied to the total synthesis of Caesalpinnone A.In this paper,resorcinol was used as the starting material to achieve the total synthesis of Caesalpinnone A with a yield of 1.028% through 12-steps reaction.Key reactions involving BINOL-phosphoric acid catalyzed [4+2] cycloaddition to construct the benzopyran skeleton structure,substrate controlled trans-selective nucleophilic substitution to achieve the relative configuration of trans,oxa-Michael addition to construct dioxatricyclo-[5.3.3.0]-tridecane bridge ring skeleton,and late-stage Photo-Fries rearrangement reaction to realize the synthesis of Caesalpinnone A.At the same time,Caesalpinnone A was tested for biological activity of human tumor cell lines including leukemia HL-60,lung cancer SMMC-7721,liver cancer A-549,breast cancer MCF-7 and colon cancer SW-480.The experimental results show that the compound has certain anticancer activity.And on this basis,it was fitted into Caesalpinnone A analogs and related activity studies were carried out.