Issue 2, 2022

Total syntheses of ericifolione and its analogues via a biomimetic inverse-electron-demand Diels–Alder reaction

Abstract

Driven by bioinspiration and appreciation of the structure of ericifolione, a biomimetic tautomerization/intermolecular inverse-electron-demand hetero Diels–Alder reaction cascade sequence promoted by sodium acetate to rapidly construct sterically hindered dihydropyran scaffolds was established, which allowed the first straightforward biomimetic total syntheses of ericifolione and its analogues with high simplicity. Moreover, this methodology set the stage for the preparation of relevant natural products or derivatives.

Graphical abstract: Total syntheses of ericifolione and its analogues via a biomimetic inverse-electron-demand Diels–Alder reaction

Supplementary files

Article information

Article type
Communication
Submitted
11 Huk 2021
Accepted
25 Huk 2021
First published
27 Huk 2021

Chem. Commun., 2022,58, 270-273

Total syntheses of ericifolione and its analogues via a biomimetic inverse-electron-demand Diels–Alder reaction

T. Zhou, A. Zheng, L. Huo, C. Li, H. Tan, S. Wang and H. Chen, Chem. Commun., 2022, 58, 270 DOI: 10.1039/D1CC06361H

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