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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.
Kiran B Manjappa, Jia-Ru Syu, Ding-Yah Yang
Organic letters 2016 Jan 15
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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.
Citation
Kiran B Manjappa, Jia-Ru Syu, Ding-Yah Yang.
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.
Organic letters.
2016 Jan 15;18(2):332-5
Mesh Tags
Catalysis
Coumarins
Cyclization
Ethers
Heterocyclic Compounds with 4 or More Rings
Isoquinolines
Light
Mesylates
Molecular Structure
Nitro Compounds
Organometallic Compounds
Pyrroles
Substances
3-nitrocoumarin
Coumarins
Ethers
Heterocyclic Compounds with 4 or More Rings
Isoquinolines
Mesylates
Nitro Compounds
Organometallic Compounds
Pyrroles
lamellarin D
lamellarin H
ytterbium(III) triflate
isoquinoline
1-methylisoquinoline
PMID: 26741300
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