Synthesis of Fijiolide A via an Atropselective Paracyclophane Formation

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


Published in:
Journal of the American Chemical Society, 137, 35, 11278–11281
Year:
2015
Publisher:
Washington, American Chemical Society
ISSN:
1520-5126
Laboratories:


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 Record created 2015-09-01, last modified 2018-03-17

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