Expedient synthesis of pyrrolo[1,2-a]indoles: preparation of the core of yuremamine.
Pyrrolo[1,2- a]indoles are conveniently prepared from tetrahydro-1,2-oxazines, which in turn are generated through the reaction of nitrones with 1,1-cyclopropanediesters. The synthetic route proves to be highly diastereoselective and provides access to the core of the recently discovered pyrrolo[1,2- a]indole natural product yuremamine.
Johansen
Michael B
MB
Department of Chemistry, The University of Western Ontario, London, Ontario, Canada.
Kerr
Michael A
MA
D003998:Dicarboxylic Acids / Q000737:chemistry; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009589:Nitrogen Oxides / Q000737:chemistry; D010078:Oxazines / Q000737:chemistry; D010936:Plant Extracts / Q000138:chemical synthesis* / Q000737:chemistry*; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D003998:Dicarboxylic Acids; D007211:Indoles; D009589:Nitrogen Oxides; D010078:Oxazines; D010936:Plant Extracts; D011758:Pyrroles; C507332:Yuremamine; C015388:nitrones; C069173:1,1-cyclopropanedicarboxylate