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Synlett 1991; 1991(2): 95-96
DOI: 10.1055/s-1991-20639
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A Regioselective Synthesis of Azafluorenone Alkaloids1

Franz Bracher*
  • *Institut für Pharmazeutische Chemie der Philipps-Universität, Marbacher Weg 6, D-3550 Marburg, Germany
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Publication Date:
07 March 2002 (online)

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6-Methoxyonychine 2 (8-methoxy-4-methyl-5H-indeno[1,2-b]pyridin-5-one) is obtained regioselectively from the biaryl 9 [2-(2-bromo-5-methoxyphenyl)-4-methyl-3-pyridinecarboxylic acid] via a Parham-type cyclisation. Alternatively, 9 can be converted to the unnatural isomer 8-methoxyonychine 11 by a simple two-step procedure (cyclisation and debromination).