Issue 16, 2024

A novel approach to the tetracyclic frameworks of anislactone-type sesquiterpenoids

Abstract

Herein, we present a novel approach to construct the A-B-C-D ring system of anislactone-type sesquiterpenoids. This innovative strategy involves a H2O2-mediated oxidative ring contraction reaction to form a 5/5 fused skeleton, while simultaneously generating contiguous quaternary carbon centers (CQCCs). Additionally, γ-lactones (A- and D-rings) are assembled through Pummerer reaction initiated cyclization and sequential Mukaiyama hydration/translactonization, respectively. Despite our efforts to introduce a hydroxyl group at C7 via C–H oxidation, these endeavors ultimately proved unsuccessful.

Graphical abstract: A novel approach to the tetracyclic frameworks of anislactone-type sesquiterpenoids

Supplementary files

Article information

Article type
Research Article
Submitted
22 May 2024
Accepted
23 Jun 2024
First published
26 Jun 2024

Org. Chem. Front., 2024,11, 4556-4559

A novel approach to the tetracyclic frameworks of anislactone-type sesquiterpenoids

L. He, X. Zhang, S. Li, X. Tian, Y. Han, H. Xie and W. Xie, Org. Chem. Front., 2024, 11, 4556 DOI: 10.1039/D4QO00915K

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