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

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...

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Bibliographic Details
Published inOrganic letters Vol. 18; no. 2; pp. 332 - 335
Main Authors Manjappa, Kiran B., Syu, Jia-Ru, Yang, Ding-Yah
Format Journal Article
LanguageEnglish
Published WASHINGTON Amer Chemical Soc 15.01.2016
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ALPHA 20-SULFATE
SYSTEM
HIV-1 INTEGRASE
TOPOISOMERASE-I
INHIBITOR
DERIVATIVES
ALKALOIDS
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.5b03524