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Five-Step Enantioselective Synthesis of Islatravir via Asymmetric Ketone Alkynylation and an Ozonolysis Cascade |
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| Authors: | 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 |
| Institution: | Department of Process Research and Development, MRL, Merck & Co., Inc., Rahway, NJ, 07065 USA |
| 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. |
| Keywords: | asymmetric alkynylation biocatalysis ozonolysis synthesis |