Facile Total Synthesis of Xanthotoxol

Abstract

Xanthotoxol, a biologically active linear furocoumarin, has been efficiently synthesized from 7‐hydroxycoumarin in six steps. The key steps included two efficient rearrangements—Fries rearrangement and Claisen rearrangement—and a Baeyer–Villiger oxidation process. The overall yield of xanthotoxol was 29%. This approach also provided a new strategy to furnish easily furocoumarins with a hydroxyl group in the framework.

Keywords:

• Baeyer–Villiger oxidation
• Claisen rearrangement
• Fries rearrangement
• furocoumarins
• total synthesis
• xanthotoxol

Acknowledgment

Financial support of the National Natural Science Foundation of China (No. 20372083) and the Natural Science Foundation of Shaanxi Province (2002B20) are gratefully acknowledged.