The Journal of Organic Chemistry

Synthetic approach to aklavinone using 2-oxo-2H-pyran-5-carboxylate (coumalate) intermediates

ME Jung, JA Hagenah

文献索引：Jung, Michael E.; Hagenah, Jeffrey A. Journal of Organic Chemistry, 1987 , vol. 52, # 10 p. 1889 - 1902

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被引用次数: 95

摘要

A novel approach for the preparation of aklavinone 5 is described in which the key step is the cycloaddition of a substituted coumalate with a ketene acetal to produce a masked A ring with the C and D rings attached. The 4-(arylmethy1) coumalate 53 was prepared from naphthalene-1, 5-diol (6) by a seven-step route involving as the key step the cyclocondensation of the methyl (arylmethy1) propiolate 52 with methyl 3-oxopentanoate ...