Synthesis of the Benzo[b]fluorene Core of the Kinamycins by Arylalkyne–Allene and Arylalkyne–Alkyne Cycloadditions

Arylalkyne–allene and arylalkyne–alkyne cycloadditions yields benzo[a]fluorenones, which are related to the tetracyclic core of the kinamycins. In the arylalkyne–alkyne cycloadditions, we found a rearrangement that produces benzo[a]fluorenones, in addition to the expected benzo[b]fluorenones. This rearrangement could be suppressed in the presence of phenol, which allowed the synthesis of 4,9-dimethoxy-2-methyl-11H-benzo[b]fluoren-11-one in excellent yield.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

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