title: A Concise Synthesis of Presilphiperfolane Core through a Tandem TMTU-Co-Catalyzed Pauson-Khand Reaction and a 6π Electrocyclization Reaction (TMTU=Tetramethyl Thiourea).
abstract: The synthesis of strained polycyclic systems from readily available precursors with a minimum number of steps and with regio- and stereochemical control constitutes an important synthetic challenge. Herein, we report a tandem reaction comprising Co-TMTU (tetramethyl thiourea)-catalyzed Pauson-Khand (PK) and 6π-electrocyclization reactions for the formation of the highly strained core of presilphiperfolanols. The developed chemistry has been applied to the total syntheses of 4-epi-presilphiperfolan-8-ol and 7-epi-presilphiperfolan-1-ol.
authors.affiliation: Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School, Shenzhen, 518055, China.
authors.forename: Zichun
authors.initials: Z
authors.lastname: Zhang
authors.affiliation: Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, Beijing National Laboratory for Molecular Science (BNLMS), College of Chemistry and Molecular Engineering.|Peking-Tsinghua Center for Life Sciences, Peking University, Beijing, 100871, China.
authors.forename: Yuanhe
authors.initials: Y
authors.lastname: Li
authors.affiliation: Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School, Shenzhen, 518055, China.
authors.forename: Dandan
authors.initials: D
authors.lastname: Zhao
authors.affiliation: Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School, Shenzhen, 518055, China.
authors.forename: Yingdong
authors.initials: Y
authors.lastname: He
authors.affiliation: Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School, Shenzhen, 518055, China.
authors.forename: Jianxian
authors.initials: J
authors.lastname: Gong
authors.affiliation: Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School, Shenzhen, 518055, China.|Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, Beijing National Laboratory for Molecular Science (BNLMS), College of Chemistry and Molecular Engineering.|Peking-Tsinghua Center for Life Sciences, Peking University, Beijing, 100871, China.
authors.forename: Zhen
authors.initials: Z
authors.lastname: Yang
mesh_terms: D002384:Catalysis; D018360:Crystallography, X-Ray; D003500:Cyclization; D008968:Molecular Conformation; D012717:Sesquiterpenes / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism; D013890:Thiourea / Q000031:analogs & derivatives* / Q000737:chemistry
chemical_list: D012717:Sesquiterpenes; C533354:presilphiperfolanol; D013890:Thiourea; C019107:tetramethylthiourea
keywords: Pauson-Khand reaction; electrocyclic reactions; presilphiperfolane core; tandem reaction; total synthesis