Preparation and synthetic applications of 2-halotryptamines: synthesis of elacomine and isoelacomine.
The preparation of 2-halotryptamines from tryptamine is described. New stereoselective intramolecular iminium ion spirocyclization methodology for the construction of spiro[pyrrolidine-3,3'-oxindoles] is outlined in synthetic studies of elacomine (1) and isoelacomine (2). [reaction: see text]
Department of Chemistry, Oregon State University, Corvallis, OR 97331, USA.
Fumiko Y
FY
Miyake
Kenichi
K
Yakushijin
David A
DA
Horne
D003500:Cyclization; D031263:Elaeagnaceae / Q000737:chemistry*; D007211:Indoles / Q000138:chemical synthesis*; D015394:Molecular Structure; D018517:Plant Roots / Q000737:chemistry; D013141:Spiro Compounds / Q000138:chemical synthesis*; D013237:Stereoisomerism
D007211:Indoles; D013141:Spiro Compounds; C487224:elacomine; C487225:isoelacomine