First syntheses of two quinoline alkaloids from the medicinal herb Ruta chalepensis via cyclization of an o-iodoaniline with an acetylenic sulfone.
The first syntheses of two quinoline alkaloids found in the medicinal herb Ruta chalepensis are reported via the conjugate addition of an o-iodoaniline to an acetylenic sulfone, followed by Pd-catalyzed carbonylation, intramolecular acylation of the corresponding sulfone-stabilized carbanion, and reductive desulfonylation.
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Thomas G
TG
Department of Chemistry, University of Calgary, Calgary, Alberta, Canada T2N 1N4. tgback@ucalgary.ca
Wulff
Jeremy E
JE
D000470:Alkaloids / Q000138:chemical synthesis*; D000480:Alkynes / Q000737:chemistry; D000814:Aniline Compounds / Q000737:chemistry; D003500:Cyclization; D018517:Plant Roots / Q000737:chemistry; D010946:Plants, Medicinal / Q000737:chemistry*; D011804:Quinolines / Q000138:chemical synthesis*; D013450:Sulfones / Q000737:chemistry
D000470:Alkaloids; D000480:Alkynes; D000814:Aniline Compounds; D011804:Quinolines; D013450:Sulfones; C023650:aniline