Substituent-oriented Diverse Synthesis Of Ortho-disubstituted Aryl Enyne Derivatives

Multi-cycle skeleton(MCS) was found in many structures of natural products,drug molecules and a variety of biological hit or lead compounds. In the past few years, because of highly structural MCS’s diversity, many synthetic approaches were developed. Among them, enyne, which has been recognized as a necessary synthon, showed great applications for synthesis of complicated MCS compounds., especially for preparing of aryl enyne, carbon-carbon double bond and triple bond derivatives, which have been extensively utilized in organic synthesis. However, synthetic methods that have been reported rarely involve multi-substituted aryl enyne synthesis. Consequently, it is necessary to develop novel and effective methods to synthesize structural diverse aryl enyne. This paper is divided into four chapters:The first chapter is the introduction. It introduces aryl enyne used in various fields, especially in complex polycyclic hydrocarbons, natural products, drugs and biological molecules synthesis applications. In the final section of this chapter several recent synthetically aryl enyne reports be summarized. We discusses their advantages and disadvantages and clear purpose and significance of this article. Chapter 2 to chapter 4 is the main content of this paper. We designed the initial synthetic routes by retrosynthetic analysis, then continue to improve the synthesis methods in practice, determining a reasonable and efficient synthetic routes. In the synthesis class Ⅱcompounds through continuous optimization to finalize the introduction of MOM protecting group can effectively achieve selective group substituted. Class Ⅲ compounds introduced different alkenyl side chain. Increase the number of substituents on the aromatic ring of class Ⅳ compounds, and in class Ⅴ compounds introduced hydroxy, halogen functional groups in order to further derivatives. Finally, seven routes are explored and applied to synthesize 17 new compounds and synthesis process for each compound are described.We describe characterize of compounds and important intermediates in this chapter with 1HNMR, 13 CNMR and NOE. The compounds that have isomers are multi-spectral analysis to determine the specific structure.