Issue 11, 2022

A concise synthesis of herbertenolide

Abstract

A concise synthesis of (±)-herbertenolide has been accomplished herein. The strategy relies on a H2O2-mediated oxidative ring contraction of all-substituted cyclic α-formyl ketones for the stereospecific construction of contiguous quaternary carbon centers (CQCCs). Furthermore, a Sc(OTf)3/chiral N,N′-dioxide catalyzed asymmetric Michael addition of benzofuranone to MVK has been optimized for forging a chiral aromatic quaternary carbon center, which enables the formal synthesis of (+)-ent-herbertenolide.

Graphical abstract: A concise synthesis of herbertenolide

Supplementary files

Article information

Article type
Communication
Submitted
07 Jan 2022
Accepted
18 Feb 2022
First published
19 Feb 2022

Org. Biomol. Chem., 2022,20, 2205-2208

A concise synthesis of herbertenolide

J. Hu, K. Ji, L. Yan, S. Yang, Y. Li, W. Wen, L. Chen, X. Wu, Y. Hu and W. Xie, Org. Biomol. Chem., 2022, 20, 2205 DOI: 10.1039/D2OB00041E

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