title: Total synthesis of taiwaniadducts B, C, and D.
abstract: The first total syntheses of taiwaniadducts B, C, and D have been accomplished. Two diterpenoid segments were prepared with high enantiopurity, both through Ir-catalyzed asymmetric polyene cyclization. A sterically demanding intermolecular Diels-Alder reaction promoted by Er(fod)3 assembled the scaffold of taiwaniadducts B and C. A carbonyl-ene cyclization forged the cage motif of taiwaniadduct D at a late stage, providing over 200 mg of this compound.
authors.affiliation: State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Lingling Road, Shanghai 200032, China.
authors.forename: Jun
authors.initials: J
authors.lastname: Deng
authors.forename: Shupeng
authors.initials: S
authors.lastname: Zhou
authors.forename: Wenhao
authors.initials: W
authors.lastname: Zhang
authors.forename: Jian
authors.initials: J
authors.lastname: Li
authors.forename: Ruofan
authors.initials: R
authors.lastname: Li
authors.forename: Ang
authors.initials: A
authors.lastname: Li
mesh_terms: D002384:Catalysis; D003500:Cyclization; D061565:Cycloaddition Reaction; D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure
chemical_list: D004224:Diterpenes; C000597632:taiwaniadduct B; C000597634:taiwaniadduct C; C000597633:taiwaniadduct D