Research On The Synthesis Of Bioactive Lamellarin U-20-Sulphate From Marine Mollusc

Lamellarin is a group of bioactive substances. The Lamellarins, first reported by Faulkner and co-workers with the isolation of Lamellarin (A~D) from the Prosobranch mollusc Lamellaria sp., have been isolated from various marine organisms including ascidians, sponges and molluscs.Lamellarin U-20-sulfate was a member of the Lamellarin family and has been shown antitumour activity (in particular, against human lung cancer) and anti-HIV (the activities of inhibiting the integrase terminal split and the chain transfer).In the light of these interesting biological activities and the difficulty in obtaining large quantities of the Lamellarins from their natural source, they had garnered a considerable amount of synthetic interest. At present, there were no reports about the synthesis of the Lamellarin U-20-Sulphate. This thesis was about the methods of synthesis the Lamellarin U-20-sulphate and some key intermediates, such as 1-(2, 4, 5-Trimethoxy-phenyl)-ethanone, 1, 2, 4-trimethoxy-5-(1-methyl-2-phenyl-vinyl)-benzene, 6, 7-Dimethoxy-1, 2, 3, 4-tetrahydro -isoquinoline, 2-Allyl-6, 7-dimethoxy-1, 2, 3, 4-tetrahydro-isoquinoline, 8, 9-Dimethoxy-5, 6-dihydro-pyrrolo [2,1-α] isoquinoline, 8, 9-Dimethoxy-pyrrolo [2,1-α] isoquinoline, and so on. The 1, 2, 4-trimethoxy-5-(1-methyl-2-phenyl-vinyl)-benzene, which was obtained by the Wittig-Horner reaction and the Gringnard reaction, was a key intermediate of synthesis various Lamellarins and a new compound. The innovation of this course, not only had a few steps and avoided using some troublesome reactions, but also had relative moderate reaction conditions and high ultimate yield.