Synthesis of Fijiolide A via an Atropselective Paracyclophane Formation

作者: Christoph Heinz , Nicolai Cramer

DOI: 10.1021/JACS.5B07964

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摘要: Fijiolide A is a secondary metabolite isolated from marine-derived actinomycete and displays inhibitory activity against TNF-α-induced activation of NFκB, an important transcription factor potential target for the treatment different cancers inflammation related diseases. glycosylated complex paracyclophane, which structurally closely to Bergman-aromatization product enediyne C-1027. We report enantioselective synthesis fijiolide demonstrating power fully intermolecular ruthenium-catalyzed [2 + 2 2]-cyclotrimerizations with three alkynes assemble heavily substituted central arene core. The characteristic strained [2.6]paracyclophane structure accessed by templated atropselective macroetherification reaction.

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