Benzyne-Furan Cycloaddition Approach to the Angucyclines: First Total Synthesis of Antibiotic C104

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Abstract
This paper describes the first total synthesis of an angucycline-class antibiotic, C104 (1), by exploiting regioselective benzyne-furan cycloaddition. Angularly fused α-siloxyfuran 3, generated in situ by treatment of butenolide 2 with NaH-TBDMSCl in THF, was directly subjected to the reaction with α-alkoxybenzyne 5, which was generated also in situ from α-iodo triflate 4. The high head-to-head selectivity in the mode of the cycloaddition enabled the regiocontrolled construction of the characteristic benz[a]-anthraquinone framework. The D-olivosyl C-glycoside was introduced via the O→C-glycoside rearrangement. This synthesis determined the absolute stereochemistry of this compound.

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