title: Visible-Light-Promoted and Yb(OTf)3-Catalyzed Constructions of Coumarin-Pyrrole-(Iso)quinoline-Fused Pentacycles: Synthesis of Lamellarin Core, Lamellarin D Trimethyl Ether, and Lamellarin H.
abstract: The efficient construction of a coumarin-pyrrole-isoquinoline-fused pentacycle via the visible-light-promoted cyclization of 4-(isoquinolin-1-ylmethyl)-3-nitrocoumarin or Yb(OTf)3-catalyzed coupling of 4-chloro-3-nitrocoumarin and 1-methylisoquinoline is reported. This methodology has further led to the development of the concise synthesis of the lamellarin core in one, two, and three steps, as well as of lamellarin D trimethyl ether in three steps.
authors.affiliation: Department of Chemistry, Tunghai University , No. 1727, Sec. 4, Taiwan Boulevard, Xitun District, Taichung City 40704, Taiwan, Republic of China.
authors.forename: Kiran B
authors.initials: KB
authors.lastname: Manjappa
authors.affiliation: Department of Chemistry, Tunghai University , No. 1727, Sec. 4, Taiwan Boulevard, Xitun District, Taichung City 40704, Taiwan, Republic of China.
authors.forename: Jia-Ru
authors.initials: JR
authors.lastname: Syu
authors.affiliation: Department of Chemistry, Tunghai University , No. 1727, Sec. 4, Taiwan Boulevard, Xitun District, Taichung City 40704, Taiwan, Republic of China.
authors.forename: Ding-Yah
authors.initials: DY
authors.lastname: Yang
mesh_terms: D002384:Catalysis; D003374:Coumarins / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D004987:Ethers / Q000138:chemical synthesis* / Q000737:chemistry; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000737:chemistry; D007546:Isoquinolines / Q000138:chemical synthesis* / Q000737:chemistry*; D008027:Light; D008698:Mesylates / Q000737:chemistry*; D015394:Molecular Structure; D009574:Nitro Compounds / Q000737:chemistry; D009942:Organometallic Compounds / Q000737:chemistry*; D011758:Pyrroles / Q000737:chemistry*
chemical_list: C446262:3-nitrocoumarin; D003374:Coumarins; D004987:Ethers; D006576:Heterocyclic Compounds, 4 or More Rings; D007546:Isoquinolines; D008698:Mesylates; D009574:Nitro Compounds; D009942:Organometallic Compounds; D011758:Pyrroles; C455554:lamellarin D; C455555:lamellarin H; C518808:ytterbium(III) triflate; C039109:isoquinoline; C103464:1-methylisoquinoline