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We describe asymmetric syntheses of the potential anti-malarial drugs (S)-2-(8-fluoro-2-methyloctyl)-3hydroxynaphthalene-1,4-dione, (S)-2-hydroxy-3-(8-trifluoromethyl-2-methyloctyl)-3-hydroxynaphthalene-1,4dione, and (S)-2-hydroxy-3-(2-methyloctyl)naphthalene-1,4-dione, which are patterned after Fieser’s “10576,” known to be active against the mosquito borne parasite Plasmodium falciparum.

Asymmetric syntheses of potential anti-malarial drugs designed from Fieser's 2-hydroxy-3-(2-methyloctyl)naphthalene-1,4-dione