With 37 million people around the world infected with HIV—and this number rising by almost 2 million a year—the search for newer, better medicines to treat this deadly disease remains an important goal. Islatravir is a nucleoside reverse transcriptase inhibitor currently undergoing clinical trials for the treatment of HIV.<br/><br/>4'-Ethynyl-2-fluoro-2'-deoxyadenosine (islatravir) is a nucleoside with two unnatural features, a fluorine atom and an ethynyl group. This talk will cover several approaches taken towards the introduction of the ethynyl group, which poses an unusual challenge, especially in view of the safety concerns around acetylene use and generation on scale. The evolution of strategies from substrate control/chiral pool approaches through asymmetric transition-metal catalysis to the final biocatalytic process will be explained.

Alkynylation adventures en route to ethynylnucleoside drug candidate islatravir

ACS Fall 2021

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