Synthesis Of Tetrahydro-β-carbolines Derivatives Via Pictet-Splengler Reactions

Synthesis of tetrahydro-β-carbolines derivatives via Pictet-Splengler reaction is studied in this thesis which is composed of three parts:Part 1:The research process of the synthesis of β-carboline alkaloids and tetrahydro-β-carboline derivatives.The β-carboline alkaloids are a large group of natural and synthetic indole alkaloids, and numerous reports investigated the biochemical and pharmacological effects of β-carboline alkaloids on the central nervous system (CNS), antitumor, antiviral, antimicrobial and antiparasitic activities. Tetrahydro-β-carbolines which are well spread in nature productions, were proved to having significant biochemical and pharmacological activities. A great amount of various synthetic methods of tetrahydro-β-carbolines have been reported.Part 2:One pot synthesis of C4 substituted tetrahydro-β-carboline derivatives via Pictet-Splengler reaction.As some of the high pharmacological valued tetrahydro-β-carboline derivatives were substituted at the C4 position, an efficient strategy to achieve this goal is needed. With very simple and readily available starting materials, we have successfully established an efficient diastereoselectivity route to the biologically important tetrahydro-β-carboline scaffold using simple base and Lewis acid catalyst, through tandem Mannich/Pictet-Splengler reactions.Part 3:Attempt asymmetric synthesis of C4 substituted tetrahydro-β-carboline derivatives.