Syntheses of the cylindrospermopsin alkaloids

descriptionPublicationkeyboard_double_arrow_right Article 01 May 2006 English Publisher:Elsevier BVJournal:Tetrahedron, volume 62, pages 4,549-4,562 (issn: 0040-4020,

Copyright policy )Funded by:NSF | Asymmetric Synthesis of a...

Authors: Ryan E. Looper; Maria T.C. Runnegar; Robert M. Williams;

doi: 10.1016/j.tet.2006.02.044

Syntheses of the cylindrospermopsin alkaloids

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Abstract

Abstract An intramolecular 1,3-dipolar cycloaddition has efficiently constructed the A-ring portions of the cylindrospermopsin alkaloids. A nitro-aldol addition of an elaborated nitroalkane to a pyrimidine aldehyde followed by an intramolecular reductive guanidinylation has enabled the syntheses of all three alkaloids in this family in 18–19 steps. We report the first asymmetric synthesis of cylindrospermopsin, unambiguously assigning its absolute configuration.

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