Scalable synthesis of (±)-gregatin A via a 1,3-dipolar cycloaddition strategy

Yiming Ding; Xiaoli Zhao; Chunlei Qu; Xianwen Long; Yaqiu Zhao; Jun Deng

doi:10.1039/D4OB02108H

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Scalable synthesis of (±)-gregatin A via a 1,3-dipolar cycloaddition strategy†

Yiming Ding,‡^ab Xiaoli Zhao,‡^a Chunlei Qu,^a Xianwen Long,^a Yaqiu Zhao^c and Jun Deng

*^a

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* Corresponding authors

^a State Key Laboratory and Institute of Elemento-Organic Chemistry, Frontiers Science Center for New Organic Matter, College of Chemistry, Nankai University, Tianjin 300071, China
E-mail: dengjun@nankai.edu.cn

^b Key Laboratory of Medicinal Chemistry for Natural Resources, Ministry of Education, Yunnan Provincial Center for Research & Development of Natural Products, School of Chemical Science and Technology, Yunnan University, Kunming, China

^c State Key Laboratory for Quality Ensurance and Sustainable Use of Dao-di Herbs, National Resource Center for Chinese Materia Medica, China Academy of Chinese Medical Sciences, Beijing, P. R. China

Abstract

A 6-step gram-scale synthesis of the fungal polyketide (±)-gregatin A is described. The synthetic route features an intermolecular 1,3-dipolar cycloaddition, a Mo-mediated disconnection of the isoxazole skeleton, and an acid-mediated deprotection/enamine hydrolysis and hemiketalization cascade.

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DOI: https://doi.org/10.1039/D4OB02108H
Article type: Communication
Submitted: 31 Dec 2024
Accepted: 09 Jan 2025
First published: 10 Jan 2025

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Org. Biomol. Chem., 2025, Advance Article

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Scalable synthesis of (±)-gregatin A via a 1,3-dipolar cycloaddition strategy

Y. Ding, X. Zhao, C. Qu, X. Long, Y. Zhao and J. Deng, Org. Biomol. Chem., 2025, Advance Article , DOI: 10.1039/D4OB02108H

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Organic & Biomolecular Chemistry

Scalable synthesis of (±)-gregatin A via a 1,3-dipolar cycloaddition strategy†

Abstract

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Scalable synthesis of (±)-gregatin A via a 1,3-dipolar cycloaddition strategy

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