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Synthesis 2008(12): 1861-1866
DOI: 10.1055/s-2008-1067085
DOI: 10.1055/s-2008-1067085
PAPER
© Georg Thieme Verlag Stuttgart · New YorkModified Mukaiyama Reaction for the Synthesis of Quinoline Alkaloid Analogues: Total Synthesis of 3,3-Diisopentenyl-N-methylquinoline-2,4-dione
Weitere Informationen
Received
20 November 2007
Publikationsdatum:
16. Mai 2008 (online)
Publikationsverlauf
Publikationsdatum:
16. Mai 2008 (online)
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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