The Study Of Synthesis Alkylated Mulberrofuran C

Mulberrofuran C belongs to Diels-Alder type compound, which was isolated from the root of mulberry plant. It showed antihypertensive activity. In this thesis, we designed a biomimetic synthesis of alkylated Mulberrofuran C from chalcone derivative and isoprene derivative by Diels-Alder reaction. Chalcone fragment was synthesised by aldol condensation, isoprene fragment was synthesised in eight steps by using selective iodination, Sonogashira reaction and Barbier reaction as key steps. Most of target compound and intermediates are new compounds and their structure was confirmed by 1H NMR and 13C NMR.Since 1980s. a lot of new Diels-Alder type compounds was isolated from mulberry plants. Biological evaluation show that these compounds have a variety of biological activities, such as antihypertensive, antimicrobial, antitumor, antiviral, hypoglycemic,inhibition of platelet aggregation, inhibition of protease C. So the Diels-Alder type compounds has attracted the interest of scientists in the field of pharmaceutical chemistry and natural medicinal chemistry. With the development and application of the new separation methods and structure identification techniques, the study of this kind of compounds is more extensive. Up to now, dozens of Diels-Alder type compounds have been found in mulberry plants.The uniqueness and novelty of this paper is the first exploration in total synthesis route at Mulberrofunan derivates. By using cheap raw materials and simple reaction conditions,We got the target product successfully. This work laid a foundation for synthesis of this kind of natural products and their derivatives. Moreover, in the future this work can help us get the strucure-activity relationships and obtain the compounds with low toxicity and good activity. In this thesis, six routes were tried to synthesize the alkylated Mulberrofuran C and we finally got the target molecule successfully.