Total Synthesis Of A New Method For The Synthesis Of High-allyl Halide And Dihydroisoquinolinium Ketone And Nahuoic Acid A's

The development of new synthetic methodologies and the total synthesis of naturalproducts are the research foci of this thesis, including:1. New method of the synthesis of homoallylic halidesHomoallylic halides have attracted a great deal of interests due to their versatilities asbuilding blocks or starting substrates in organic synthesis and in thepharmaceutical/agrochemical industries. In the presence of diethyl phosphite, cyclopropylGrignard reagents react with carbonyl compounds to give homoallylic bromides in goodyields. A plausible mechanism has thus been proposed, based on the study of reactionintermediates.2. The synthesis of dihydro IsoquinolinoneIsoquinolines have wide range of biological properties, including vasodilation, anti-tumor,etc. Themolecular diversity, synthesis and biological activity of these compounds havebeen extensively investigated and still remain the ongoing interests in pharmaceuticalchemistry. In the presence of Pd(CH3CN)2Cl2, silver carbonate and DIPEA,N-methoxybenzamides react with allene compounds via selective C-H functionalization toproduce dihydroisoquinolinone derivatives in good yields.3. Total synthesis of polyketide natural product Nahuoic acid ANahuoic acid A is a complex polyketide produced in culture by a Streptomyces sp.obtained from tropical marine sediment. Nahuoic acid A shows significant biologicalactivities, is the first known selective SAM-competitive inhibitor of SETD8. We havedeveloped an effective, convergent synthetic plan for the synthesis of this molecule, andsome important intermediates have been successfully obtained.