title: Stereoselective total synthesis of (+)-licochalcone E.
abstract: The synthesis of (+)-licochalcone E (1) was accomplished for the first time in 13 steps from aryl bromide (6) with 8% overall yield. Palladium-catalyzed Negishi-Reformatsky coupling reaction of compound 6 with ethyl 2-(tributylstannyl)acetate provided the aryl acetic ester (5), which was converted to aryl acetamide (4) via mixed anhydride formation. Chiral auxiliarymediated methylation of the (S)-4-benzyl-2-oxazolidinone-derived aryl acetamide (4) provided the key asymmetric benzylic methyl group in compound 1.
authors: College of Pharmacy and Research Institute of Drug Development, Chonnam National University, Gwangju 500-757, Korea.
authors: Zhiguo
authors: Z
authors: Liu
authors: Zengtao
authors: Z
authors: Wang
authors: Goo
authors: G
authors: Yoon
authors: Seung Hoon
authors: SH
authors: Cheon
mesh_terms: D002384:Catalysis; D047188:Chalcones / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D023303:Oxazolidinones / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D047188:Chalcones; D023303:Oxazolidinones; C520147:licochalcone E; D010165:Palladium