title: Total synthesis of aphadilactones A-D.
abstract: The first total synthesis of aphadilactones A-D, diastereomeric natural products recently isolated from the Meliaceae plant Aphanamixis grandifolia by Yue and co-workers, which possess an unprecedented carbon skeleton, has been achieved. The synthesis features a catalytic asymmetric hetero-Diels-Alder reaction to form the dihydropyran ring, concurrent installation of the lactone and furan moieties via a tandem acid-catalyzed acetal cleavage, oxidation, and cyclization process, and an intermolecular Diels-Alder reaction to forge the target products.
authors: State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University , Lanzhou 730000, PR China.
authors: Jian-Peng
authors: JP
authors: Yin
authors: Min
authors: M
authors: Gu
authors: Ying
authors: Y
authors: Li
authors: Fa-Jun
authors: FJ
authors: Nan
mesh_terms: D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification; D002384:Catalysis; D003500:Cyclization; D061565:Cycloaddition Reaction; D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification; D010084:Oxidation-Reduction; D013237:Stereoisomerism
chemical_list: D001688:Biological Products; D004224:Diterpenes; D005663:Furans; D007783:Lactones