Synthetic Studies Of Indole Alkaloids Arborisidine And Subincanadine C

This dissertation compassed the following three parts:(1)review of monoterpene indole alkaloids;(2)synthetic studies of indole alkaloid Arborisidine;(3)synthetic studies of indole alkaloid Subincanadine C.Part?: The classification,physiological activities,separation and some classic synthetic reports of monoterpene indole alkaloids were briefly introduced.Part?: We used tryptamine and 2,3-pentanedione as the starting materials to get the key tetracyclic intermediate 2-91 through Pictet–Spengler reaction,Grignard reagent addition reaction and aza-Cope/Mannich rearrangement reaction.Then the method of oxidative coupling developed by Prof.Dawei Ma was used as the key step to finish the synthesis of natural product Arborisidine.Now this part of work is still under further exploration.Part ?: Enlightened by the above work,we started the synthetic studies of Subincanadine C.Firstly,we tried to gain Subincanadine C from the key tetracyclic intermediate 2-91'.However,some unexpected failure happened,so we adjusted the synthetic sequences.We used 2,3-butanedione as the original ketone instead of 2,3-pentanedione through the same process to get another key tetracyclic intermediate 3-43.And then we hope to oxidize a hydroxyl group at the alpha position of the carbonyl group by the Rubottom oxidation reaction,following by a Wittig reaction,and complete the synthesis of Subincanadine C through a SN2 substitution reaction.Now this part of work is still under further exploration.