International Union of Pure and Applied Chemistry

Evolution-based synthesis of racemic alkaloids*

M.J. Wanner and G.J. Koomen

Amsterdam Institute of Molecular Studies, Nieuwe Achtergracht 129, 1018 WS Amsterdam, The Netherlands
E-mail: [email protected]

Abstract: Many of the alkaloids found in Nitraria and Lupine species can be envisaged to arise from two simple building blocks, namely tryptamine and tetrahydropyridine. In particular in the nitraria species, the alkaloids occur as racemates in some cases, despite the presence of many stereocenters. We assume that racemic alkaloids might be formed without interference of enzymes via spontaneous reactions of highly reactive intermediates. By carrying out a biomimetic approach many of these alkaloids were obtained by us via chemical synthesis, based on this concept of reactive precursors. The paper discusses the preparation of racemic Lupinine, Spartein and Nitraramine from tryptamine and the trimer of tetrahydropyridine, based on imine-enamine chemistry. Preliminary biomimetic studies on the synthesis of Manzamines and Ingenamines from 3-alkylpyridinium dimers are reported.

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