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Pure Appl. Chem., Vol. 70, No. 11,
pp. 2129, 1998
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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* Invited lecture presented at the International
Conference on Bioversity and Bioresources: Conservation and
Utilization, 23-37 November 1997, Phuket, Thailand.
Page last modified 27 April 1999.
Copyright ©1997, 98, 99 International Union of Pure and Applied
Chemistry.
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