Total Synthesis of Fijiolide A
Keywords:[2 2 2] cycloaddition, Fijiolide, Glycosylation, Paracyclophane formation, Total synthesis
AbstractFijiolide A is a secondary metabolite isolated from a marine-derived actinomycete of the genus Nocardiopsis. It was found to significantly reduce the TNF-? induced activity of the transcription factor NF?B, which is considered a promising target for the treatment of cancer and inflammation-related diseases. We disclose an enantioselective synthesis of fijiolide A enabled by a fully intermolecular, yet regioselective cyclotrimerization of three unsymmetrical alkynes to construct its tetra-substituted arene core. An atropselective macroetherification enables the assembly of the strained [2.6]paracyclophane motif. A late-stage glycosylation of the macrocyclic aglycone at its tertiary alcohol position allowed for the first total synthesis of fijiolide A.
How to Cite
C. Heinz, N. Cramer, Chimia 2016, 70, 258, DOI: 10.2533/chimia.2016.258.
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