Preparation of a Key Intermediate En Route to the Anti-HIV Drug Lenacapavir.
Juan C CaravezYuting HuErfan OftadehKirubel T MamoBruce H LipshutzPublished in: The Journal of organic chemistry (2024)
A very efficient four-step synthesis of the main fragment of Gilead's anti-HIV drug lenacapavir is described. The route showcases a 1,2-addition to an intermediate aldehyde using an organozinc halide derived from a commercially available difluorobenzyl Grignard reagent. This sets the stage for the oxidation of the resulting secondary alcohol to the desired ketone, which relies solely on catalytic amounts of TEMPO together with NaClO as the terminal oxidant, affording the targeted ketone in 67% overall yield.
Keyphrases
- antiretroviral therapy
- hiv positive
- hiv testing
- hiv infected
- human immunodeficiency virus
- hepatitis c virus
- hiv aids
- men who have sex with men
- adverse drug
- cancer therapy
- emergency department
- south africa
- hydrogen peroxide
- drug induced
- mass spectrometry
- nitric oxide
- high resolution
- alcohol consumption
- simultaneous determination