| Chrysotricine(l) is a novel β-carboline alkaloid isolated from Chinese herb medicine Hedyotis chrysotricha. It contains a 2,5-transtetrahydrofuranyl group on the 1-position of β-carboline. Preliminary pharmaceutical study shows that it can inhibite the growth of HL-60 cells. In order to further study its activity and to determine its absolute configuation, the synthesis of chrysotricine was achieved in this thesis.The total synthesis of ( ± ) chrysotricine and its epimer was achieved from tryptophan by a direct and concise route.Reagents: a: CH3CHO, IN H2SO4 b: 10% K2Cr2O7, HOAc c: 1)n-BuLi, 2) Compound 37 d :MCPBA, HOAc. e: CH3I f: 10% NaOHThe cyclization of compound 35 was also studied. When compound 35 was... |