An Efficient and Sustainable Synthesis of the Antimalarial Drug Tafenoquine

Rahul D Kavthe; Joseph R A Kincaid; Bruce H Lipshutz

doi:10.1021/acssuschemeng.2c05628

An Efficient and Sustainable Synthesis of the Antimalarial Drug Tafenoquine

ACS Sustain Chem Eng. 2022 Dec 19;10(50):16896-16902. doi: 10.1021/acssuschemeng.2c05628. Epub 2022 Dec 7.

Authors

Rahul D Kavthe¹, Joseph R A Kincaid¹, Bruce H Lipshutz¹

Affiliation

¹ Department of Chemistry & Biochemistry, University of California, Santa Barbara, California 93106, United States.

Abstract

An 11-step, 8-pot synthesis of the antimalarial drug tafenoquine succinate was achieved in 42% overall yield using commercially available starting materials. Compared to the previous manufacturing processes that utilize environmentally egregious organic solvents and toxic reagents, the current route features a far greener (as measured by Sheldon's E Factors) and likely more economically attractive sequence, potentially expanding the availability of this important drug worldwide.