Studies On The Synthesis Of (-)-EGCG And SFN, X-Ray And Gram Scale Synthesis Of 3,6-DCC

This thesis is concerned with the synthesis of natural products (-)-Epigallocatechin-3-gallate [(-)-EGCG] and Sulforaphane (SFN), also including gram scale synthesis and crystal structure of 3,6-DCC based on the reported method. It mainly consists of the following four parts:First, the development of the Mitsunobu reaction was reviewed, in which the mechanism of this reaction were introduced briefly. Particularly, the application of Mitsunobu reaction in organic synthetic chemistry was summarized in present.In chapter 2, a concise and efficient route for the total synthesis of natural product (-)-EGCG including a facile and green synthesis of SFN was presented. In the process of syntheis of (-)-EGCG, the key steps involved Sharpless AD, intramolecular and intermolecular Mitsunobu reactions. This procedure was more convenient than that reported in the literature. And we were confident that it would be applied in the synthesis of other natural products belong to the family of (-)-EGCG very well. Next, the simple synthesis of SFN was reported based on the reported procedure. This procedure was friendly to our surrouding and answered for the atom economic theory. The present work was also of great important significance for clinical investigation of this compound.In chapter 3, gram scale synthesis of 3,6-DCC was optimized based on the reported methods. And its crystal structure including its precursor was first reported, not only to supply a gap of these data on these compounds in literatures, but the intermolecular interactions could been explained clearly.In chapter 4, Cyclphane 4-1 was designed and its synthesis was explored. The reactions involved to this procedure were simple correspondingly, but this kind of moleculars were very important. If this route could be used successfully, we were confident that it could be applied to the family of this compound very well.