Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

Total Synthesis of Kanamienamide and Clarification of Biological Activity

Total Synthesis of Kanamienamide and Clarification of Biological Activity
Arihiro Iwasaki, Kiyotake Suenaga, Daisuke Ojima
The total synthesis of kanamienamide, an enamide with an enol ether and an 11-membered macrolactone of marine origin, was achieved. The synthesis features the construction of an enamide adjacent to an enol ether by Buchwald amidation and an 11-membered ring by Mitsunobu lactonization. In addition, on the basis of the biological assay of synthetic 1, we clarified that kanamienamide (1) was not an apoptosis-like cell death inducer, as reported in the isolation paper, and revealed its real biological activity as a necrosis-like cell death inducer.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b02288

DOI: 10.1021/acs.joc.7b02288

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