Five-Step Enantioselective Synthesis of Islatravir via Asymmetric Ketone Alkynylation and an Ozonolysis Cascade.
Niki R PatelMark A HuffmanXiao WangBangwei DingMark McLaughlinJustin A NewmanTeresa AndreaniKevin M MaloneyHeather C JohnsonAaron M WhittakerPublished in: Chemistry (Weinheim an der Bergstrasse, Germany) (2020)
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.