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

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

Org Biomol Chem. 2025 Jan 16. doi: 10.1039/d4ob02108h. Online ahead of print.

Authors

Yiming Ding^{1

2}, Xiaoli Zhao¹, Chunlei Qu¹, Xianwen Long¹, Yaqiu Zhao³, Jun Deng¹

Affiliations

¹ State Key Laboratory and Institute of Elemento-Organic Chemistry, Frontiers Science Center for New Organic Matter, College of Chemistry, Nankai University, Tianjin 300071, China. [email protected].
² 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, 650091, China.
³ 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, 100700, P. R. China.

PMID: 39817840
DOI: 10.1039/d4ob02108h

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.