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Synthesis 1997; 1997(5): 567-572
DOI: 10.1055/s-1997-1222
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Synthesis of Azabenzisochromanequinone Antibiotics, II: 9(6)-Hydroxy-6(9)-Azabenzisochromanequinones via Aminoisochromanes and Meldrum's Acid

Carsten Tödter, Helmut Lackner*
  • *Institut für Organische Chemie der Universität Göttingen, Tammannstraße 2, D-37077 Göttingen, Germany, Fax +49(551)399660
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Publication Date:
31 December 2000 (online)

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The synthesis of 6(7)-amino-5,8-dimethosyisochromanes 7,8, precursors of the B-C ring system of benzisochromanequinone antibiotics 1, is described. Subsequent N-alkylation using Meldrum's acid/trimethyl orthoformate followed by a high temperature cyclization and oxidative demethylation yields 9(6)-0-demethyl-6(9)-azaeleutherins 13 and 6(9)-azaepinanaomycin A methyl esters 14. The novel aza-analogues allowed further studies on the structure-activity relations in the field of (aza)benzisochromanequinone antibiotics.

antibiotics - azabenzisochromanequinones - annulation of pyridine systems to isochromanequinones - structure-activity relations