Journal
SYNTHETIC COMMUNICATIONS
Volume 37, Issue 1-3, Pages 361-367Publisher
TAYLOR & FRANCIS INC
DOI: 10.1080/00397910601038616
Keywords
baeyer-Villiger oxidation; Claisen rearrangement; Fries rearrangement; furocoumarins; total synthesis; xanthotoxol
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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 BaeyerVilliger 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.
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