Synthesis Of Stilbene - Phenanthroline And Its Analogues

Diphenyl ethylene-phenylpropanoid lignan is an important stilbene compound, which is reported showing anti-tumor activity and hypoglycemic activity in MTT screening. There is few research of these compounds to be reported because of no total synthesis except low yield biomimetic synthesis, which restricts the in-depth study of this class of compounds. This paper attempt to construct benzocycloalkyl structure using the Michael addition reaction, which establish a quick and simple method to synthesis of diphenyl ethylene-phenylpropanoid lignan analogs.In the first chapter, summarizes the research progress of podophyllotoxin in recent years, simultaneously on the structural modification of podophyllotoxin.In chapter2, In order to increase the yield Michael addition reaction in synthesis of podophyllotoxin, many reaction conditions to be screened about the reaction time, temperature, protecting groups and donor acceptor ratio, etc. The protect group of acceptor was found, which is (2’6-di-tert-butyl-4-methoxy-anisole) with more steric effect.In chapter3, the conjugate addition reaction of aryl lithium towards cinnamic BHA protected a’(3-unsaturated ester were studied, using chiral auxiliary group construction benzylic stereoisomers asymmetric center. Total synthesis of non-peptide analogs of endothelin antagonists Enrasentan and a key five-membered ring structure construction are successfully finished. Total synthesis of diphenyl ethylene-phenylpropanoid lignin was studied based on the Michael addition reaction.Experiment procedure, physical data for compounds described in Chapter2and Chapter3are presented in Chapter4.