Five‐Step Enantioselective Synthesis of Islatravir via Asymmetric Ketone Alkynylation and an Ozonolysis Cascade
Niki R. Patel, Mark A. Huffman, Xiao Wang, Bangwei Ding, Mark McLaughlin, Justin A. Newman, Teresa Andreani, Kevin M. Maloney, Heather C. Johnson, Aaron M. Whittaker
Abstract
A 5-step enantioselective synthesis of the potent anti-HIV nucleoside islatravir is reported. The highly efficient route was enabled by a novel enantioselective alkynylation of an α,β-unsaturated ketone, a unique ozonolysis-dealkylation cascade in water, and an enzymatic aldol-glycosylation cascade.
Topics & Concepts
Enantioselective synthesisCascadeOzonolysisAlkynylationKetoneChemistryCombinatorial chemistryOrganic chemistryCatalysisChromatographyCyclopropane Reaction MechanismsAsymmetric Hydrogenation and CatalysisSynthesis and Catalytic Reactions