Total Synthesis of (±)- and (+)-Euphohyrisnoid A

Zhanhong YeSouthern University of Science and Technology

Qiao-Qiao AoGuangxi Normal University

Yang-Chao PengSouthern University of Science and Technology

Xin LiuShenzhen University

X. Sheldon LinSouthern University of Science and Technology

Chuang‐Chuang LiGuangxi Normal University

Journal of the American Chemical Society·February 6, 2026

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Abstract

The first total synthesis of (±)- and (+)-euphohyrisnoid A, a highly rearranged lathyrane <i>Euphorbia</i> diterpenoid with a new [5-7-6-6] tetracyclic core, was accomplished. The synthesis was strategically guided by a mild intramolecular Diels-Alder (IMDA) reaction, which efficiently constructed the pivotal bicyclo[2.2.2] ring system with high diastereoselectivity. This outcome experimentally validated prior quantum mechanical calculations. The IMDA precursor was assembled efficiently via a Tsuji-Trost reaction. The desired seven stereocenters, including two quaternary stereocenters in the final product, were constructed diastereoselectively.

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