Synthetic Study Toward The 6/8/6 Core Skeleton Of Taxol

As one of the key steps of the research and exploitation of natural products,total synthesis of bioactive natural products has been one of the most important fields of organic chemistry for a long time.Taxol,which is studied in this dissertation,is a notable member of the bioactive taxane diterpenoid family.Due to its complicated structure and impressive biological activities,chemists and biologists have paid a lot of concern on it since its first discovering.Taxol showed great antitumor bioactivities and has been used in the clinical treatment of many kinds of cancers,especially ovarian carcinoma,breast cancer for decades.Taxol is structured with a complicated and distinctive [6/8/6] tricyclic ring system,which is gifted with a high tension due to its eight-membered-ring and bridge-head double bond.The molecule has overall eleven chiral centers including three quaternary carbon chiral centers,which also makes a large contribution to the difficulty of the total synthesis of taxol.Because of its impressive biological activities and highly challenging molecular structure,taxol has been a research focus of many scientists for several decades.This paper includes a brief conclusion of the total synthesis,formal synthesis and industrial producting ways of taxol,as well as the synthetic research of other taxane family molecules.Based on the summary of precedent researches,we hope to develop a concise synthetic route with high efficiency to obtain the [6/8/6] core skeleton of taxol.The whole plan is to utilize the convergent synthesis strategy to construct the core skeleton of the natural product through intramolecular Diels-Alder reaction,which is promising to increase the efficiency of the synthesis of taxol.Meanwhile,we desire to acquire the right chirality of the taxol core skeleton by feasible molecular design.In this study,we have already prepared the synthetic precursors and connected them with coupling reactions,intramolecular Diels-Alder reaction is applied for the synthesis of the core skeleton of taxol,of which the chirality is the same as the natural taxol molecules,making a solid foundation for our challenge to the total synthesis of taxol.