Modified Mukaiyama Reaction for the Synthesis of Quinoline Alkaloid Analogues: Total Synthesis of 3,3-Diisopentenyl-N-methylquinoline-2,4-dione

Lamprini C. Zikou; Olga Igglessi-Markopoulou

doi:10.1055/s-2008-1067085

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Modified Mukaiyama Reaction for the Synthesis of Quinoline Alkaloid Analogues: Total Synthesis of 3,3-Diisopentenyl-N-methylquinoline-2,4-dione

Lamprini C. Zikou, Olga Igglessi-Markopoulou*
Laboratory of Organic Chemistry, Department of Chemical Engineering, National Technical University of Athens, Zografou Campus, 15780 Athens, Greece
Fax: +30(21)07723072; e-Mail: ojmark@orfeas.chemeng.ntua.gr;

Abstract

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Abstract

A general synthetic approach, capable of accessing a diverse range of 3,3-disubstituted quinoline-2,4-diones and 1,8-naphthyridine-2,4-diones via titanium tetrachloride catalyzed C-acylation of silyl ketene acetals is described. The suggested methodological platform is surveyed using different reaction conditions and is applied to the total syntheses of 3,3-diisopentenyl-N-methylquinoline-2,4-dione and 3-demethyl-N-methylatanine.

Key words

Lewis acids - fused-ring systems - aldol reactions - quinolines - natural products

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