Synthesis of lamellarin U and lamellarin G trimethyl ether by alkylation of a deprotonated alpha-aminonitrile.
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.
Liermann
Johannes C
JC
Institut für Organische Chemie, Universität Mainz, Mainz, Germany.
Opatz
Till
T
D000478:Alkylation; D003374:Coumarins / Q000138:chemical synthesis* / Q000737:chemistry; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000737:chemistry; D007546:Isoquinolines / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D009570:Nitriles / Q000737:chemistry*; D013055:Spectrophotometry, Infrared
D003374:Coumarins; D006576:Heterocyclic Compounds, 4 or More Rings; D007546:Isoquinolines; D009570:Nitriles; C486059:lamellarin G trimethyl ether