Total Synthesis of Isoflavones: Jamaicin, Calopogonium Isoflavone-B, Pseudobaptigenin, and Maxima Substance-B. Friedel-Crafts Acylation Reactions with Acid-Sensitive Substrates

Article abstract of DOI:10.1021/jo00386a014

The Friedel-Crafts acylation reaction was studied on several acid-sensitive substrates.Under the proper conditions of varying Lewis acids, solvents, and reaction temperatures, the acylation indeed took place, thus obviating the necessity for functional group protection-deprotection sequences.By use of these procedures, the naturally occuring isoflavones jamaicin (1), calopogonium isoflavone-B (2), maxima substance-B (30), and pseudobaptigenin (31) were synthesized and characterized.