Synthesis Of1,1-diaryl-2-alkenyl Type Natural Compounds

Thel,1-diaryl-2-alkenyl core was existed extensively in the structure of various types of natural products, such as procyanidines, latifolin, Cassumunins, and Calyxin B. These analogues have been studied fairly extensively and have been shown to exhibit various biological properties including anti-fungus, anti-inflammatory, anti-virus, anti-oxidant and anti-cancer. This thesis aims at the studies on the synthesis of1,1-diaryl-2-alkenyl analogues latifolin and cassumunin C via a general and efficient approach, which may provide good help for the synthesis and biological studies of these natural products and their analogues.It mainly consists of the following two parts:1. Synthetic study on the efficient construction of the basic skeleton of1,1-diaryl-2-alkenyl core:we used a general propargylation for construction of the core by using iodine as a cheap and eco-friendly catalyst. Natural product latifolin have been synthesized in10%overall yield based on the propargylation. In addition, antioxidative effects of latifolin was also studied by DPPH method and we concluded that the antioxidant mechanism of curcumin is a H-atom abstraction from the phenolic group, not from the benzhydryl group.2. Synthetic study of the natural product Cassumunin C:the first total synthesis of Cassumunin C has been accomplished in10%overall yield. The general propargylation was applied successfully to the construction of the1,1-diaryl-2-alkynyl core and a high selective hydrogenation was used to construction of the trans-form carbon-carbon double bond in Cassumunin C.