Synthesis of a Simple Model Compound of Dynemicin and Cycloaromatization with Pinacol-Pinacolone Rearrangement in the Strained Enediyne Medium Ring.

Novel bicyclo[7.3.1]-tridecadiyne system included in dynemicin was synthesized from a quinoline aldehyde in 9 steps. Key step was the cyclization with silyl acetylene to ketone carbonyl group through fluoride activation with CsF. The cyclized compound did aromatize under acidic condition, with opening of the epoxide ring, to give a Bergman product that was further converted with pinacol-pinacolone rearrangement.

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