Five‐Step Enantioselective Synthesis of Islatravir via Asymmetric Ketone Alkynylation and an Ozonolysis Cascade. Issue 62 (1st October 2020)

• Record Type: Journal Article
• Authors: Patel, Niki R.; Huffman, Mark A.; Wang, Xiao; Ding, Bangwei; McLaughlin, Mark; Newman, Justin A.; Andreani, Teresa; Maloney, Kevin M.; Johnson, Heather C.; Whittaker, Aaron M.
• Is Part Of: Chemistry. Volume 26:Issue 62(2020)
• Page Start: 14118
• Page End: 14123
• Publication Date: 2020-10-01
• Subjects: asymmetric alkynylation -- biocatalysis -- ozonolysis -- synthesis; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.202003091
• Languages: English
• ISSNs: 0947-6539

Abstract

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. Abstract : Asymmetric catalysis : 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.