6533b83afe1ef96bd12a71ee
RESEARCH PRODUCT
Synthesis of Lamellarin U and Lamellarin G Trimethyl Ether by Alkylation of a Deprotonated α-Aminonitrile
Johannes C. LiermannTill Opatzsubject
Magnetic Resonance SpectroscopyAlkylationSpectrophotometry InfraredNitrileStereochemistryOrganic ChemistryEtherNuclear magnetic resonance spectroscopyAlkylationIsoquinolinesHeterocyclic Compounds 4 or More RingsChemical synthesisMass Spectrometrychemistry.chemical_compoundDeprotonationchemistryCoumarinsNitrilesProtecting groupBischler–Napieralski reactiondescription
1,2,3,4-Tetrahydroisoquinoline-1-carbonitriles can serve as starting materials for the one-pot synthesis of 5,6-dihydropyrrolo[2,1 a]isoquinolines and 1-benzyl-3,4-dihydroisoquinolines. The latter compounds were transformed to lamellarin G trimethyl ether and lamellarin U in short reaction sequences. This method allows the introduction of acid-sensitive protecting groups for the phenolic hydroxy functions which would be cleaved under the harsh conditions of the classical Bischler-Napieralski reaction.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2008-05-24 | The Journal of Organic Chemistry |