Studies On The Asymmetric Syntheses Of Cryptocaryone And Cryptochinone F

This dissertation is on the studies of the asymmetric syntheses of dihydrochalcone Cryptocaryone and tetrahydroflavanone Cryptochinone F. It consisted of the following three parts:Chapter1. The synthetic approaches used for the construction of a—alkylidene—γ—butyrolactones motif and it’s application in the total synthesis of natural products.(Review). Many natural products contain a—alkylidene—γ—butyrolactones motif. This review summarizes the structural types, synthetic method and its application in the total synthesis of these natural products.Chapter2. Studies on the asymmetric synthesis of Cryptocaryone.The work of our group in synthesis of dihydropyrone natural product Cryptocaryone was introduced briefly. An efficient total synthesis of cryptocaryone from natural quinic acid was described.Chapter3. Studies on the asymmetric synthesis of Cryptochinone F.The work of our group in synthesis of tetrahydroflavanone natural product Cryptochinone F was introduced briefly. An efficient total synthesis of Cryptochinone F from natural quinic acid was described. The synthesis features a Mukaiyama aldol reaction, a TfOH-assisted dihydropyrone formation, and a one pot saponification/lactonizaton/1.6-oxa-Michael addition sequences as key steps.