Pictet-Spengler reaction of biogenic amines with (2 R)- N-Glyoxyloylbornane-10,2-sultam. Enantioselective synthesis of ( S)-(+)- N-methylcalycotomine

(2 R)- N-Glyoxyloylbornane-10,2-sultam reacted with dopamine hydrochloride, forming the Pictet-Spengler condensation product, which was further converted into ( S)-(+)- N)-methylcalycotomine of high enantiomeric purity. The same kind of reaction with tryptamine hydrochloride gave the condensation pr...

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Bibliographic Details
Published in:Tetrahedron: asymmetry 1995-12, Vol.6 (12), p.2899-2902
Main Authors: Czarnocki, Zbigniew, Mieczkowski, Józef B., Kiegiel, Jaroslaw, Araźny, Zbigniew
Format: Article
Language:English
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Summary:(2 R)- N-Glyoxyloylbornane-10,2-sultam reacted with dopamine hydrochloride, forming the Pictet-Spengler condensation product, which was further converted into ( S)-(+)- N)-methylcalycotomine of high enantiomeric purity. The same kind of reaction with tryptamine hydrochloride gave the condensation product with 100% d.e. Graphic
ISSN:0957-4166
1362-511X
DOI:10.1016/0957-4166(95)00380-0