Total synthesis of two novel 5,6,7,8-tetrahydroindolizine alkaloids, polygonatines A and B |
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| Authors: | Dinsmore Andrew Mandy Karen Michael Joseph P |
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| Institution: | Molecular Sciences Institute, School of Chemistry, University of the Witwatersrand, Johannesburg, P.O. Wits 2050, South Africa. |
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| Abstract: | The structures of polygonatines A and B, two simple but structurally novel alkaloids, have been substantiated by synthesis. Cyclisation of 4-(1H-pyrrol-1-yl)butanoic acid or its ethyl ester produced 6,7-dihydroindolizin-8(5H)-one , formylation of which at C-3 followed by reduction afforded polygonatine A . Acetylation of this alkaloid followed by displacement of the acetate with ethanol yielded polygonatine B , possibly via an azafulvenium cation. |
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