Four‐Component Construction of Coumarin‐Fused Pyrrolo[2,1‐<i>a</i>]isoquinoline: Expedient Synthesis of Lamellarins and Their Regioselective Demethylation
Kiran B. Manjappa, Jia‐Wei Jhang, K. C. Seetha Lakshmi, Ding‐Yah Yang
Abstract
Abstract Construction of the coumarin‐fused pyrrolo[2,1‐ a ]isolquinoline skeleton was realized through a four‐component reaction between isoquinoline, ethyl bromoacetate, o ‐hydroxybenzaldehyde and nitromethane. This methodology was further extended to the synthesis of lamellarin D trimethyl ether and a formal synthesis of lamellarin D. The controlled demethylation of lamellarin D trimethyl ether yielded dihydroxy and tetrahydroxy lamellarin analogues regioselectively.
Topics & Concepts
IsoquinolineChemistryRegioselectivityDemethylationEtherStereochemistryNitromethaneCoumarinEthyl bromoacetateOrganic chemistryCatalysisGeneDNA methylationGene expressionBiochemistrySynthesis and Characterization of PyrrolesSynthesis and Reactivity of HeterocyclesPorphyrin and Phthalocyanine Chemistry