SYNTHETIC STUDIES ON BIOLOGICALLY ACTIVE TRYPTOPHAN METABOLITES.

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1. Eudistomins. Marine alkaloids, eudistomin H, I, and P (1) have been synthesized from tryptamine and proline. Eudistomine C, F. L and debromoeudistomin L (2) which have a oxathiazepine ring and a tetrahydro-B- carboline ring and display anti-virus activity, have been synthesized as the first time from N-hydroxytryptamine and D-cysteinal.2. Flustramines : 3a-(1,1-dimethylpropargyl)pyrrolo 2,3-b indole (3) has been prepared by the reaction of tryptamine carbamate and propargylalcolhol Co-complex in the presence of a Lewis acid.3. The 4,5,6-tribromo-3-indoleacetamide (4) which is the indole moiety of chartelline, was prepared from the cyclic tautomer of 3-indoleacetamide.4.12alpha- and 12beta-Fumitremorgin C (5) has been prepared from the intermediate to fumitremorgin B.5. Optically active 1-substituted-1 2,3,4-tetrahydro-beta-carbolines (6) have been prepared by the asymmetic reduction of 1-substituted-3,4-dihydro-beta-carbolines with moderate optical purity.