Bioinspired concise synthesis of caged Sesquiterpenoids Artatrovirenols A and B

Yunxia Yang; Dong Xie; Liang Huo; Yue Liu; Jinbo Duan; Huilin Li; Pan-Pan Zhou; Xingang Xie; Xuegong She

doi:10.1038/s41467-024-55560-9

Bioinspired concise synthesis of caged Sesquiterpenoids Artatrovirenols A and B

Nat Commun. 2025 Jan 2;16(1):322. doi: 10.1038/s41467-024-55560-9.

Authors

Yunxia Yang¹, Dong Xie¹, Liang Huo¹, Yue Liu¹, Jinbo Duan¹, Huilin Li¹, Pan-Pan Zhou¹, Xingang Xie², Xuegong She³

Affiliations

¹ State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, 730000, Gansu, PR China.
² State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, 730000, Gansu, PR China. [email protected].
³ State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, 730000, Gansu, PR China. [email protected].

Abstract

Artatrovirenols A and B are two newly isolated sesquiterpenoids with a complex caged framework. We report herein a concise synthesis of artatrovirenols A and B in 9 and 8 steps, respectively. The complex caged tetracycle is rapidly constructed from a known planar guaiane-type precursor through a bioinspired intramolecular [4 + 2] cyclization to firstly access artatrovirenol B, which is further transformed into artatrovirenol A through a biomimetic epoxidation-mediated lactonization reaction. This synthesis establishes a concise asymmetric approach to access artatrovirenols A and B, and also provides insightful evidence to their biogenetic pathway in nature.

Abstract

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