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Paper | Special issue | Vol 79, No. 1, 2009, pp.831-850
Published online, 25th November, 2008
DOI: 10.3987/COM-08-S(D)51
Syntheses and Absolute Configuration Assignments of Mono- and Di-substituted Chiral Quinoline Alkaloids Obtained by Asymmetric Oxidation

Derek R. Boyd,* Narain D. Sharma, Stephen A. Barr, and Pui L. Loke

*School of Chemistry and Chemical Engineering, The Queen's University of Belfast, David Keir Kuilding, Belfast, BT9 5AG, U.K.

Abstract

Mono- and di-substituted quinoline, 2-quinolone, dihydrofuroquinoline and dihydropyranoquinoline alkaloids have been synthesised with enantiomeric excess values of > 90%, via asymmetric epoxidation, or asymmetric dihydroxylation of the corresponding alkene precursors. The absolute configurations of isobalfourodine, ψ-balfourodine, ψ-isobalfourodine, isobalfourodinium methiodide, balfourolone, hydroxylunidine, orixine, nororixine, isopteleflorine, O-acetylisopteleflorine, O-methylhydroxylunium methiodide and hydroxylunine have been rigorously determined by a combination of circular dichroism spectroscopy, ozonolysis, and stereochemical correlation. Of these, the absolute configurations of six alkaloids were previously unknown and six were assigned incorrect configurations in the literature.