Journal
ORGANIC LETTERS
Volume 22, Issue 12, Pages 4659-4664Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.0c01431
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The synthesis of the potent anti-HIV investigational treatment islatravir is described. The key step in this synthesis is a highly enantioselective catalytic asymmetric alkynylation of a ketone. This reaction is a rare example of the asymmetric addition of an alkyne nucleophile to a ketone through ligand-accelerated catalysis that was performed on a greater than 100 g scale. By leveraging a multienzyme cascade, a highly diastereoselective aldol-glycosylation was used to complete the target in eight steps.
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