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Communication | Regular issue | Vol 71, No. 2, 2007, pp.245-252
Published online, 26th December, 2006
DOI: 10.3987/COM-06-10937
An Improved Pictet-Spengler Condensation: A convenient Synthetic Route to Bioactive Manzamine Derivatives

Yeun-Mun Choo and Mark T. Hamann*

*Department of Pharmacognosy, Chemistry and Biochemistry and National Center for Natural Products Research, School of Pharmacy, University of Mississippi, University, Mississippi 38677, U.S.A.

Abstract

An improved Pictet-Spengler method for the construction of a modified β-carboline moiety from an α,β-unsaturated aldehyde is described. The Pictet-Spengler reactions between ircinal A (1) and tryptamine derivatives under milder conditions have resulted in shorter reaction times and higher product yields (70 to 89%) with control of stereochemistry. The Pictet-Spengler products (9 and 11) are two new manzamine alkaloids, which display strong activities against Mycobacterium intracellulare with IC50 values of 0.2 and 0.06 μg/mL, respectively.