Synthesis Of Diarylheptanoids

Diarylheptanoid is a group of compounds which firmly bears the 1,7-diphenylheptane skeleton as a special characteristics in natural product estate. They have become of interest in natural product research because of their remarkable anti-cancer, anti-microbial and anti-oxidant activity. This thesis is mainly focused on synthetic studies of 7 naturally occurring diarylheptanoids. The following four parts are mainly included:1. The first chapter introduced the structural features, classification isolation and biological activities of diarylheptanoids. Based on their structural characteristics,the biomimetic syntiiesis of diarylheptanoids were proposed.2. The diarylheptanoid natural products,(-)-de-O-methylcentrolobine and(+)-Centrolobol,was first isolated from the heartwoods of centrolobium robustum and have significant anti-inflammatory. A concise and effieient total synthesis of those two natural plant metabolites was aehieved for the first time starting from commercially available D-Mannitol, featuring in a iodine mediated prins cyclizations reaction, wittig reaction and ring-opening reduction. Meanwhile, synthesis of compound 1-33 and 1-34 have been attempted.3. Diosniponol A and B were isolated by Kang Ro Lee and co-workers from rhizomes of D. nipponica. Enantioselective total synthesis of diosniponol B has been achieved starting from compound 2-72. Accordingly, diosniponol A was accessed from diosniponol B through an inversion reaction.4. The diarylheptanoid, rhoiptelol B, the structure of which contains a tetrahydropyran ring, was isolated from the fruits of Rhoiptelea chiliantha in 1996. One atom-economic approache was designed for the synthetic study of natural rhoiptelol B. Finally, one isomer of rhoiptelol B was achieved.