Total Synthesis Of Indole Aikaloid (±)-Subincanadine E And Synthesis Studies Of Aominine And Tubingensin A

This thesis mainly focuses on synthetic studies of indole alkaloid subincanadine E, aominine and carbazole alkaloids tubingensin A, which includes the following two parts:Chapter 1:Total synthesis of (±)-subincanadine E.Natural products subincanadines were isolated from the bark of the Brazilian medicinal plant Aspidosperma subincanum Mart by Kobayashi and co-workers. Among these products, subincanadine E, also named pericine, was first isolated from Picralima nitida cell suspension cultures by Joachim Stockigt in 1982. Subincanadine E was found to have cytotoxicity against murine lymphoma L1210 cells and human epidermoid carcinoma KB cells based on in vitro preliminary biological experiments. In this chapter, the previous synthetic studies toward subincanadines have been reviewed briefly. Subsequently, the first total synthesis of subincanadine E was described, which commenced from tryptamine hydrochloride salt and key features included Ni(COD)2-mediated intramolecular Michael addition and zinc-mediated fragmentation reaction.Chapter 2:Synthetic studies of aominine and tubingensin A.Indole diterpenoid anomine and carbazole alkaloid tubingensin A were isolated from the sclerotia of the fungus by Gloer in1989, and display insecticidal and antiviral activity. In this chapter, the previous synthetic studies toward anomine and tubingensin A have been reviewed briefly. Then our synthetic approach for the total synthesis about tubingensin A and anomine were described, which incloud three different routes with enyne cyclization or diyne cyclization, intermolecular Diels-Alder reaction and intramolecular Friedel-Crafts alkylation as key steps respectively.