title: Total synthesis of absinthin.
abstract: (+)-Absinthin, a structurally unique triterpene, has been efficiently constructed in nine reaction steps and in 18.6% overall yield from O-acetylisophotosantonic lactone. The synthesis features Mitsunobu arylselenylation, oxidative elimination of allylic arylselenides, biomimetic dimerization via regio- and stereospecific Diels-Alder reaction, and a four-step stereochemical inversion of a highly sterically congested tertiary alcohol. This approach has not only tackled the formidable synthetic challenges in assembling structurally complex (+)-absinthin but also paved an efficient synthetic route to a series of medicinally attractive absinthin analogues.
authors.affiliation: Laboratory of Modern Synthetic Organic Chemistry and State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, China 200032.
authors.forename: Weihe
authors.initials: W
authors.lastname: Zhang
authors.forename: Shengjun
authors.initials: S
authors.lastname: Luo
authors.forename: Fang
authors.initials: F
authors.lastname: Fang
authors.forename: Qingshou
authors.initials: Q
authors.lastname: Chen
authors.forename: Hanwei
authors.initials: H
authors.lastname: Hu
authors.forename: Xueshun
authors.initials: X
authors.lastname: Jia
authors.forename: Hongbin
authors.initials: H
authors.lastname: Zhai
mesh_terms: D031171:Artemisia absinthium / Q000737:chemistry*; D045789:Sesquiterpenes, Guaiane / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D045789:Sesquiterpenes, Guaiane; C499475:absinthin