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Total Synthesis of Antimalarial Macrolide Strasseriolide A by Ni/Zr-Mediated Reductive Ketone Coupling
Atsushi Umehara1, Ko-Hei Kawakita1, Makoto Sasaki1
1Graduate School of Life Sciences, Tohoku University, 2-1-1 Katahira, 980-8577 Aoba-ku, Sendai, Japan.
Abstract:
The total synthesis of the antimalarial macrolide strasseriolide A is described. We established two different synthetic approaches. The first approach involves intermolecular esterification and a challenging Ni/Zr/Cr-mediated reductive ketone coupling macrocyclization for the formation of the 18-membered ring. The second approach involves intermolecular Ni/Zr-mediated reductive ketone coupling and macrolactonization. Ni-catalyzed C(sp3)-C(sp2) cross-coupling of a vinyl halide with an alkyl halide was employed for fragment synthesis.
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