Synthesis Of Subincanadines Alkaloid

Subincanadine F,a novel quaternary indole alkaloids,possessing an unprecedented azobicyclo[4.3.1]undecane framework,was isolated from the bark of the Brazilian medicinal plant.The first part of this dissertation describes our studies towards the total synthesis Subincanadine F.First in the process of synthesis tetracyclic ketone of Subincanadine F,we found a novel tandem reaction of tert-butyl 5-chloro-2,3-dioxopen tanoate(1-12)with primary amine,this reaction can be used concisely for synthesis 6.5-azobiccyclic compounds in one step.The in fluence of elect ron element of aromatic nucleus has been studied systematically.The possi ble mechanism was proposed based on experimental results.In order to avoiding the trouble of deprotection.Tryptamine was used as the starting material to construct compound(1-50),olefin fragment has been connected via crossing couple.For gener ating azoniacycle,two ways were explored.Then tryptamine was used as the starting material to construct the tetr acyclic ketone via protection indole with PMB,Michael addition,Pic tet-S pengler reaction and Dieckmann condensation.Attaching a side chain to th e carbonyl group at this stage has been proved unfruitful...