Total Synthesis of (+)-Nimbolide

Keywords

(+)-nimbolide - limonoids - Pd-catalyzed borylative Heck cyclization - Pd-catalyzed enolate cross-coupling - stereoretentive etherification - radical cyclization - lactonization

Significance

Sarlah and co-workers report the convergent total synthesis of ( + )-nimbolide in 11 steps (longest linear sequence). This natural product has shown promising biological activities regarding the reduction of certain cancer hallmarks, such as cancer metastasis, cancer-related inflammation and angiogenesis.

 

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Comment

The authors developed a borylative Heck cyclization to access trans-decalin scaffold C, using a carvone-derived precursor A. Further adjustments of the oxygenation pattern furnished building block J. Epoxidation followed by stereoretentive ring-opening by alcohol K furnished ether L. Final radical cyclization and lactonization gave the natural product ( + )-nimbolide.

 

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Publikationsverlauf

Artikel online veröffentlicht:
23. Juni 2025