title: Expeditious synthesis ofcis-1-methyl-2, 3,3a,4,5,9b-hexahydro-1H-pyrrolo-[3,2h]isoquinoline / [2,3-f]quinolineviaazomethine ylide-alkene [3+2] cycloaddition.
abstract: Expeditious syntheses ofcis-1-methyl-2,3,3a,4,5,9b-hexahydro-1H-pyrrolo-[3,2h]isoquinoline /[2,3-f]]quinoline have been developed. The syntheses started with commercially available material and afforded excellent overall yields in straightforward steps. Intramolecular azomethine ylide-alkene [3+2] cycloaddition is the key step in the construction of these pyrroloisoquinoline and pyrroloquinoline scaffolds. This route is much more atom-economic than those reported in the literature and appropriate for scale-up synthesis.
authors.affiliation: College of Pharmacy, University of Kentucky, Lexington, KY 40536, USA.
authors.forename: Zhenfa
authors.initials: Z
authors.lastname: Zhang
authors.forename: Linda P
authors.initials: LP
authors.lastname: Dwoskin
authors.forename: Peter A
authors.initials: PA
authors.lastname: Crooks
keywords: Azomethine ylide; Nicotine analog synthesis; [3+2] cycloaddition
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