Additive-controlled asymmetric iodocyclization enables enantioselective access to both α- and β-nucleosides

Qi Wang, Jiayi Mu, Jie Zeng, Linxi Wan, Yangyang Zhong, Qiuhong Li, Yitong Li, Huijing Wang () and Fener Chen ()
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Qi Wang: Sichuan University
Jiayi Mu: Sichuan University
Jie Zeng: Wuhan Institute of Technology
Linxi Wan: Sichuan University
Yangyang Zhong: Sichuan University
Qiuhong Li: Sichuan University
Yitong Li: Sichuan University
Huijing Wang: Sichuan University
Fener Chen: Sichuan University

Nature Communications, 2023, vol. 14, issue 1, 1-12

Abstract: Abstract β-Nucleosides and their analogs are dominant clinically-used antiviral and antitumor drugs. α-Nucleosides, the anomers of β-nucleosides, exist in nature and have significant potential as drugs or drug carriers. Currently, the most widely used methods for synthesizing β- and α-nucleosides are via N-glycosylation and pentose aminooxazoline, respectively. However, the stereoselectivities of both methods highly depend on the assisting group at the C2’ position. Herein, we report an additive-controlled stereodivergent iodocyclization method for the selective synthesis of α- or β-nucleosides. The stereoselectivity at the anomeric carbon is controlled by the additive (NaI for β-nucleosides; PPh3S for α-nucleosides). A series of β- and α-nucleosides are prepared in high yields (up to 95%) and stereoselectivities (β:α up to 66:1, α:β up to 70:1). Notably, the introduced iodine at the C2’ position of the nucleoside is readily functionalized, leading to multiple structurally diverse nucleoside analogs, including stavudine, an FDA-approved anti-HIV agent, and molnupiravir, an FDA-approved anti-SARS-CoV-2 agent.

Date: 2023
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DOI: 10.1038/s41467-022-35610-w

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