What question did this study set out to answer?

To achieve the first total synthesis of (±)- and (+)-euphohyrisnoid A with high precision in structure.

February 8, 2026

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

Key Points

To achieve the first total synthesis of (±)- and (+)-euphohyrisnoid A with high precision in structure.
Utilized a mild intramolecular Diels-Alder (IMDA) reaction for bicyclo[2.2.2] ring construction.
Employed a Tsuji-Trost reaction to assemble the IMDA precursor.
Focused on constructing seven stereocenters, including two quaternary stereocenters, with high diastereoselectivity.
Successfully synthesized both (±)- and (+)-euphohyrisnoid A.
Achieved efficient construction of the bicyclo[2.2.2] ring system.
Validated quantum mechanical calculations through experimental outcomes.

Abstract

The first total synthesis of (±)- and (+)-euphohyrisnoid A, a highly rearranged lathyrane Euphorbia 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 bicyclo2.2.2 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.

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

Key Points

Abstract

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