RSC Publishing


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Cover image for Journal of Chemical Research, click here for current issue

Journal of Chemical Research

From January 2000, the monthly Journal of Chemical Research has been owned and published by Science Reviews Ltd.




Paper

J. Chem. Res. (S), 1999, 94 - 95, DOI: 10.1039/a808999j


Experiments towards the Synthesis of the Ergot Alkaloids and Related Structures.Part 7.1 Novel Syntheses of some 4-Acyl-2,3,4,4a,5,6-hexahydrobenzo[f]quinolin-2-ones

Mark A. E. Bowman and Ralph E. Bowman


Reaction of the N-formyl enol-lactone 4 and the corresponding N-acetyl 10 and N-methoxycarbonyl 11 derivatives with bis(trimethylsilyl)potassiomalonate in THF at 60°C followed by treatment with aqueous sodium hydrogen carbonate and cyclisation as above, yielded the 4-formyl-, 4-acetyl- and 4-methoxycarbonyl-tricyclic ketones 7, 13 and 14 in yields of 31, 35 and 36%, respectively.