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Paper | Regular issue | Vol 55, No. 3, 2001, pp.495-503
Published online, 1st January, 1970
DOI: 10.3987/COM-00-9107
Synthesis of Xestomanzamines A and B

Brigitte E. A. Burm, Peter Blokker, Edwin Jongmans, Erwin van Kampen, Maritn J. Wanner, and Gerrit-Jan Koomen*

*Laboratory of Organic Chemistry, Institute of Molecular Chemistry, University of Amsterdam, Nieuwe Achtergracht 129, 1018 WS Amsterdam, The Netherlands

Abstract

Synthetic pathways are described for the synthesis of two naturally occurring β-carbolines, xestomanzamine A and B. The synthesis of aromatic xestomanzamine A was most conveniently achieved by way of a Grignard reaction in dichloromethane. This route is suitable for the synthesis of analogues with modifications in the imidazole ring of xestomanzamine A. Xestomanzamine B, an oxidation-sensitive dihydro-β-carboline, was prepared by Pictet-Spengler condensation of tryptamine with a vicinal tricarbonyl substituted imidazole.