Total Synthesis of Fijiolide A

Fijiolide A is a secondary metabolite isolated from a marine-derived actinomycete of the genus Nocardiopsis. It was found to significantly reduce the TNF-alpha induced activity of the transcription factor NF kappa 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.


Published in:
Chimia, 70, 4, 258-262
Year:
2016
Publisher:
Bern, Schweizerische Chemische Gesellschaft
ISSN:
0009-4293
Keywords:
Laboratories:




 Record created 2016-07-19, last modified 2018-03-17


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