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The study aims to develop two distinct synthetic routes to produce the antimalarial compound strasseriolide A.

March 29, 2026The Journal of Organic Chemistry0 citationsOpen Access

Total Synthesis of Antimalarial Macrolide Strasseriolide A by Ni/Zr-Mediated Reductive Ketone Coupling

AUAtsushi UmeharaTohoku University KKKo-hei KawakitaTohoku University MSMakoto SasakiTohoku University

Key Points

The study aims to develop two distinct synthetic routes to produce the antimalarial compound strasseriolide A.
Developed two synthetic approaches to strasseriolide A
Employed Ni/Zr/Cr-mediated reductive ketone coupling for macrocyclization
Utilized Ni-catalyzed C(sp³)-C(sp²) cross-coupling for fragment synthesis
Implemented intramolecular esterification and macrolactonization techniques.
Successfully synthesized strasseriolide A through both methods
The Ni/Zr-mediated coupling facilitated the formation of the 18-membered ring
Intermolecular approaches showed efficiency in fragment synthesis.

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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