Construction of the Tetracyclic Skeleton of Polycyclic Norcembranoids Sinudenoids B–D Via Ireland-Claisen Rearrangement

作者：Xiaofei Gao, Hui Shen, Peng Chen, Liang Huo, Huilin Li, Xingang Xie, Gaoyuan Zhao, Xuegong She · 发表于：The Journal of Organic Chemistry · 年份：2025 · DOI：10.1021/acs.joc.5c00317 · 被引用次数：3 · 研究领域：Marine Sponges and Natural Products、Advanced Synthetic Organic Chemistry、Plant-based Medicinal Research

Sinudenoids B-D represent a biologically significant and structurally intricate family of natural products distinguished by their unique [5-5-6-6] tetracyclic skeleton. Herein, we present an efficient strategy for the asymmetric synthesis of their [5-5-6-6] tetracyclic framework. Key features of our approach include a convergent synthetic strategy driven by esterification, a pivotal Ireland-Claisen rearrangement to construct a C11-C12 bond, followed by efficient lactonization and isomerization, and a ring-closing metathesis to complete the [5-5-6-6] tetracyclic skeleton.