title: Total synthesis of ent-(+)-cinanthrenol A.
abstract: The first total synthesis of ent-(+)-cinanthrenol A of potent estrogenic activity was achieved with 10.9% overall yield in 13 steps from commercially available materials. Our synthesis features a photo-promoted oxidative 6π-electron electrocyclization/aromatization for construction of the cyclopenta[a]phenanthren-17-one and Furukawa hydroxyl-directed cyclopropanation for the rare spiro[2,4]heptane. The brevity of this synthetic strategy would allow an expedited access to cinanthrenol A and its analogs for further biological evaluation.
authors.affiliation: Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong, China.
authors.forename: Liangyu
authors.initials: L
authors.lastname: Zhu
authors.affiliation: Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong, China.
authors.forename: Rongbiao
authors.identifier: 0000-0002-2740-5222
authors.initials: R
authors.lastname: Tong
mesh_terms: D003500:Cyclization; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010616:Phenanthrenes / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013256:Steroids / Q000138:chemical synthesis*
chemical_list: D010616:Phenanthrenes; D013256:Steroids; C000588617:cinanthrenol A; C000614357:cyclopenta(a)phenanthren-17-one