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Synlett 1997; 1997(3): 313-315
DOI: 10.1055/s-1997-758
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A New Two-Step Synthesis of Quinolone Alkaloids Based on the Regioselective Addition of Organometallic Reagents to 4-Silyloxyquinolinium Triflates

Uwe Beifuss* , Sabine Ledderhose
  • *Institut für Organische Chemie, Georg-August-Universität Göttingen, Tammannstr. 2, D-37077 Göttingen, Germany, Fax: +49(551)39-9660
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Publikationsdatum:
31. Dezember 2000 (online)

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Organolithium- as well as Grignard reagents regioselectively add to N-protected 4-silyloxyquinolinium triflates with yields ranging from 38 to 93 %; the Cbz-protected C-2 adducts are easily transformed in a single operation to give the corresponding 2-substituted 4-quinolones in nearly quantitative yields.

qunolinium triflates - silyl enol ether - C-2 addition - organometallic reagents - quinolone alkaloid