Total synthesis of xanthohumol.
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.
Khupse
Rahul S
RS
Center for Drug Design and Development, College of Pharmacy, The University of Toledo, Toledo, Ohio 43606-3390, USA.
Erhardt
Paul W
PW
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
D047309:Flavones; D005419:Flavonoids; D011427:Propiophenones; C104536:xanthohumol