Synthetic Studies Towards Salvianolic Acid A And Dimeric Xanthone Natural Product Rugulotrosin A

This dissertation is mainly focused on the synthetic studies toward natural product salvianolic acid A and dimeric xanthone natural product rugulotrosin A.Salvia miltiorrhizae is a traditional Chinese medicinal material prepared by drying the roots of the dicotyledonous plant Salvia miltiorrhiza Bunge.The injection of watersoluble ingredients of Salvia miltiorrhiza is used to treat coronary heart disease,angina pectoris,acute myocardial infarction and other diseases.Salvianolic acid A is one of the effective compounds isolated from the water-soluble components of Salvia miltiorrhiza.We have developed a unified synthetic route to synthesize natural product salvianolic acid A.By preparing a phenol triflate compound and olefin compound,we completed Mizoroki–Heck coupling reaction,then Knoevenagel condensation reaction converted it into α,β-unsaturated carboxylic acid compound.After the α,β-unsaturated carboxylic acid compound is condensed with the chiral hydroxyl molecule,the natural product salvianolic acid A can be efficiently prepared by hydrolyzing the methyl ester and removing the protective group.Rugulotrosin A is a dimeric xanthone natural product isolated from the Penicillium sp.of soil samples from Sussex,Australia.It has significant antibacterial activity against some Gram-positive bacteria.By developing and improving the Knoevenagel condensation/6π electronic cascade reaction,we can efficiently construct the tricyclic skeleton of xanthone.In this step,using a chiral substrate can induct oxa-quaternary carbon center generate a single configuration.After exploring the aromatization reaction,the adjustment of the benzylic oxidation state,and the synthesis of iodine compounds,we finally obtained the monomer compound,and completed the formal synthesis of rugulotrosin A.