Synthesis and derivatization of 8-acetylpsoralens. Acetyl migrations during Claisen rearrangement

…, D Kanne, JD Frazier, H Rapoport

Index: Bender; Kanne; Frazier; Rapoport Journal of Organic Chemistry, 1983 , vol. 48, # 16 p. 2709 - 2719

Full Text: HTML

Citation Number: 38

Abstract

We have synthesized a series of 8-acetylpsoralens in which methyl and hydrogen substitutions were systematically varied at the 4-and 5'-positions. Claisen rearrangement was employed in developing the furano ring, and acetyl migration during the rearrangement was identified as a major side reaction. This migration was circumvented by applying a diethylaluminum chloride catalyzed Claisen rearrangement to the pyrone ring-opened ...