Modular ketal-linked prodrugs and biomaterials enabled by organocatalytic transisopropenylation of alcohols

Na Yu, Yang Xu, Tao Liu, Haiping Zhong, Zunkai Xu, Tianjiao Ji, Hui Zou, Jingqing Mu, Ziqi Chen, Xing-Jie Liang, Linqi Shi, Daniel S. Kohane () and Shutao Guo ()
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Na Yu: Nankai University
Yang Xu: Nankai University
Tao Liu: Nankai University
Haiping Zhong: Nankai University
Zunkai Xu: Nankai University
Tianjiao Ji: Children’s Hospital Boston, Harvard Medical School
Hui Zou: Nankai University
Jingqing Mu: Nankai University
Ziqi Chen: Nankai University
Xing-Jie Liang: Guangzhou Medical University
Linqi Shi: Nankai University
Daniel S. Kohane: Children’s Hospital Boston, Harvard Medical School
Shutao Guo: Nankai University

Nature Communications, 2021, vol. 12, issue 1, 1-11

Abstract: Abstract Isopropenyl ethers are critical intermediates for accessing medicinally valuable ketal-based prodrugs and biomaterials, but traditional approaches for the synthesis of isopropenyl ethers suffer from poor functional group compatibility and harsh reaction conditions. Here, we develop an organocatalytic transisopropenylation approach to solve these challenges, enabling the synthesis of isopropenyl ethers from various hydroxyl-group-containing small-molecule drugs, polymers, and functional building blocks. The method provides a straightforward and versatile synthesis of isopropenyl ethers, features excellent tolerance of diverse functional groups, applies to a wide range of substrates, and allows scalable synthesis. The development of this organocatalytic transisopropenylation approach enables access to modular preparation of various acid-sensitive ketal-linked prodrugs and functionalized ketalated biomaterials. We expect our syntheses and transformations of isopropenyl ethers will find utility in several diverse fields, including medicinal chemistry, drug delivery, and biomaterials.

Date: 2021
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Persistent link: https://EconPapers.repec.org/RePEc:nat:natcom:v:12:y:2021:i:1:d:10.1038_s41467-021-25856-1

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DOI: 10.1038/s41467-021-25856-1

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