title: Total Synthesis of Epoxyeujindole A.
abstract: The total synthesis of epoxyeujindole A, a structurally unusual indole diterpenoid isolated from Eupenicillium javanicum, has been accomplished for the first time. The synthesis features a late-stage cationic cyclization strategy, which took advantage of an electron-rich olefinic substrate. The CDE ring system was assembled via an enantioselective conjugate addition/alkylation, a Luche cyclization, and a Nozaki-Hiyama-Kishi reaction. The heavily substituted A ring was constructed through a Suzuki-Miyaura coupling and a cationic cyclization, and the bridged fused B ring was formed through a Prins reaction.
authors.affiliation: State Key Laboratory of Bioorganic and Natural Products Chemistry, Collaborative Innovation Center of Chemistry for Life Sciences, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Lingling Road, Shanghai 200032, China.
authors.forename: Zhaohong
authors.initials: Z
authors.lastname: Lu
authors.affiliation: State Key Laboratory of Bioorganic and Natural Products Chemistry, Collaborative Innovation Center of Chemistry for Life Sciences, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Lingling Road, Shanghai 200032, China.
authors.forename: Hailong
authors.initials: H
authors.lastname: Li
authors.affiliation: State Key Laboratory of Bioorganic and Natural Products Chemistry, Collaborative Innovation Center of Chemistry for Life Sciences, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Lingling Road, Shanghai 200032, China.
authors.forename: Ming
authors.initials: M
authors.lastname: Bian
authors.affiliation: State Key Laboratory of Bioorganic and Natural Products Chemistry, Collaborative Innovation Center of Chemistry for Life Sciences, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Lingling Road, Shanghai 200032, China.
authors.forename: Ang
authors.initials: A
authors.lastname: Li
mesh_terms: D003500:Cyclization; D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D055324:Eupenicillium / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation
chemical_list: D004224:Diterpenes; C000609226:epoxyeujindole A