title: Total synthesis of (-)-jiadifenin.
abstract: As easy as ABCD: (-)-Jiadifenin was synthesized in eighteen reaction steps from 1-[(E)-(4'-bromo-2'-butenyl)oxy]-4-methoxybenzene. Key features of this synthesis include: 1) Ireland-Claisen rearrangement to produce the two contiguous quaternary centers at C5 and C6 simultaneously, 2) intramolecular Pauson-Khand reaction (IMPKR) to concurrently construct the A and B rings, and 3) [2+2] photo-cycloaddition to generate the all-carbon quaternary center at C9.
authors.affiliation: Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, China.
authors.forename: Yang
authors.initials: Y
authors.lastname: Yang
authors.forename: Xingnian
authors.initials: X
authors.lastname: Fu
authors.forename: Jianwei
authors.initials: J
authors.lastname: Chen
authors.forename: Hongbin
authors.initials: H
authors.lastname: Zhai
mesh_terms: D061565:Cycloaddition Reaction; D029523:Illicium / Q000737:chemistry*; D008958:Models, Molecular; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D012717:Sesquiterpenes; C457979:jiadifenin