Studies On The Asymmetric Total Syntheses Of Morphine Analogues:(-)-9-epi-Metazocine,(-)-Pentazocine And(-)-Eptazocine

This dissertation aims at the Asymmetric total syntheses of morphine analogues:(-)-9-epi-metazocine,(-)-pentazocine and (-)-eptazocine; and also study on the total syntheses of heliespirones B and C. It consisted of the following three parts:Chapter1. Hypervalent iodine-mediated phenol dearomatization in natural product synthesis (Review)Described the introduction and applications of "hypervalent iodine-mediated phenol dearomatization" in natural products syntheses.Chapter2. Asymmetric total syntheses of morphine analogues:(-)-9-epi-metazocine,(-)-pentazocine and (-)-eptazocineWe have finished the total synthesis of (-)-9-epi-metazocine using radical cyclization as key step. We also constructed benzobicyclo skeleton via aza-Prins cyclization and intramolecular Friedel-Crafts reaction. Based on the stragegy, we have finished the total synthesis of (-)-pentazocine and (-)-eptazocine.Chapter3. Asymmetric syntheses of heliespirones B and CSyntheses of heliespirones B and C used methyl2-p-tolylacetate as starting material and Evans alkylation, hypervalent iodine-mediated phenol dearomatization as key steps.