190278-37-6Relevant articles and documents
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
Manjappa, Kiran B.,Syu, Jia-Ru,Yang, Ding-Yah
, p. 332 - 335 (2016)
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-methylisoqu
Construction of Pentacyclic Lamellarin Skeleton via Grob Reaction: Application to Total Synthesis of Lamellarins H and D
Manjappa, Kiran B.,Lin, Jhih-Min,Yang, Ding-Yah
, p. 7648 - 7656 (2017/07/26)
An efficient construction of phenyl-substituted coumarin-pyrrole-isoquinoline-fused pentacycle via base-promoted Grob-type coupling of 3-nitrocoumarin and papaverine in a sealed tube is reported. This reaction is further applied to the total synthesis of lamellarin H in three linear steps and lamellarin D in eight linear steps with overall yields of 31% and 14%, respectively.
Total syntheses of lamellarin D and H. The first synthesis of lamellarin-class marine alkaloids
Ishibashi, Fumito,Miyazaki, Yuka,Iwao, Masatomo
, p. 5951 - 5962 (2007/10/03)
Total syntheses of marine polyaromatic alkaloids, lamellarin D (1) and H (2), are described. The pentacyclic lamellarin ring system was constructed by N-ylide mediated pyrrole ring formation and subsequent lactonization of 4 obtained by an assembly of known benzylisoquinoline 5, benzoate 6 and ethyl bromoacetate.