Highly stereoselective [4 + 3] cycloadditions of nitrogen-stabilized oxyallyl cations with pyrroles: an approach to parvineostemonine.
[structure: see text]. A highly stereoselective [4 + 3] cycloaddition of N-substituted pyrroles with allenamide-derived nitrogen-stabilized chiral oxyallyl cations is described here. This method provides an approach for constructing tropinone alkaloids.
Antoline
Jennifer E
JE
Division of Pharmaceutical Sciences and Department of Chemistry, University of Wisconsin, Madison, Rennebohm Hall, Madison, WI 53705, USA.
Hsung
Richard P
RP
Huang
Jian
J
Song
Zhenlei
Z
Li
Gang
G
D000470:Alkaloids / Q000138:chemical synthesis / Q000737:chemistry; D000498:Allyl Compounds / Q000737:chemistry*; D001952:Bridged-Ring Compounds / Q000138:chemical synthesis / Q000737:chemistry; D002412:Cations / Q000737:chemistry; D018360:Crystallography, X-Ray; D008958:Models, Molecular; D015394:Molecular Structure; D009584:Nitrogen / Q000737:chemistry*; D011758:Pyrroles / Q000737:chemistry*; D013141:Spiro Compounds / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism
D000470:Alkaloids; D000498:Allyl Compounds; D001952:Bridged-Ring Compounds; D002412:Cations; D011758:Pyrroles; D013141:Spiro Compounds; C519469:parvineostemonine; D009584:Nitrogen