TY - JOUR
T1 - Total Synthesis of Kanamienamide and Clarification of Biological Activity
AU - Ojima, Daisuke
AU - Iwasaki, Arihiro
AU - Suenaga, Kiyotake
N1 - Funding Information:
This work was supported by JSPS KAKENHI Grant Number 16H03285. We thank the Kaneka Corporation for their gift of (S)-Roche ester.
PY - 2017/12/1
Y1 - 2017/12/1
N2 - 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.
AB - 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.
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U2 - 10.1021/acs.joc.7b02288
DO - 10.1021/acs.joc.7b02288
M3 - Article
C2 - 29083171
AN - SCOPUS:85036622747
VL - 82
SP - 12503
EP - 12510
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 23
ER -