title: Total synthesis of xanthohumol.
abstract: The total synthesis of xanthohumol (1) was accomplished in 10% overall yield from phloracetophenone after six steps. Insertion of a prenyl group onto the aryl ring was achieved by a para-Claisen rearrangement after using a Mitsunobu reaction to establish the key prenyl ether precursor. A Claisen-Schmidt condensation was deployed to construct the chalcone scaffold followed by removal of MOM protecting groups under acidic conditions that were optimized to prevent concomitant cyclization to the flavone.
authors.affiliation: Center for Drug Design and Development, College of Pharmacy, The University of Toledo, Toledo, Ohio 43606-3390, USA.
authors.forename: Rahul S
authors.initials: RS
authors.lastname: Khupse
authors.forename: Paul W
authors.initials: PW
authors.lastname: Erhardt
mesh_terms: D003500:Cyclization; D047309:Flavones / Q000737:chemistry*; D005419:Flavonoids; D027582:Humulus / Q000737:chemistry; D015394:Molecular Structure; D010946:Plants, Medicinal / Q000737:chemistry; D011427:Propiophenones / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D047309:Flavones; D005419:Flavonoids; D011427:Propiophenones; C104536:xanthohumol