Synthesis of (+/-)tylophorine by the intramolecular cycloaddition of an azide with an [omega]-chloroalkene
dc.contributor.author | Pearson, William H. | en_US |
dc.contributor.author | Walavalkar, Rajesh | en_US |
dc.date.accessioned | 2006-04-10T18:30:37Z | |
dc.date.available | 2006-04-10T18:30:37Z | |
dc.date.issued | 1994 | en_US |
dc.identifier.citation | Pearson,, William H., Walavalkar, Rajesh (1994)."Synthesis of (+/-)tylophorine by the intramolecular cycloaddition of an azide with an [omega]-chloroalkene." Tetrahedron 50(43): 12293-12304. <http://hdl.handle.net/2027.42/31955> | en_US |
dc.identifier.uri | http://www.sciencedirect.com/science/article/B6THR-42HNRSK-2Y/2/f3bb4fd70c98aac3b2abee16160f175e | en_US |
dc.identifier.uri | https://hdl.handle.net/2027.42/31955 | |
dc.description.abstract | Cyclization of (Z)-1-(2-chloromethyl)phenyl-5-azidopent-1-ene 10 in benzene at 120[deg]C followed by treatment with sodium borohydride produced 1,2,3,5,10,10a-hexahydropyrrolo[1,2-b]isoquinoline 11 in 71% yield. A similar cyclization of (Z)-2,3,6,7-tetramethoxy-9-(5-azido-1-pentenyl)-10-chloromethylphenanthrene 3 gave the phenanthroindolizidine alkaloid (+/-)- tylophorine 5 in 82% yield. These reactions proceed by intramolecular 1,3-dipolar cycloaddition of the azide onto the alkene followed by loss of nitrogen from the triazoline intermediate to give an imine The imine is N-alkylated in situ by the pendant benzyl chloride to provide an iminium ion, which is reduced by sodium borohydride to afford the indolizidines. The synthesis of (+/-)-tylophorine was acomplished in 11 steps from homoveratric acid in 5% overall yield. | en_US |
dc.format.extent | 996375 bytes | |
dc.format.extent | 3118 bytes | |
dc.format.mimetype | application/pdf | |
dc.format.mimetype | text/plain | |
dc.language.iso | en_US | |
dc.publisher | Elsevier | en_US |
dc.title | Synthesis of (+/-)tylophorine by the intramolecular cycloaddition of an azide with an [omega]-chloroalkene | en_US |
dc.type | Article | en_US |
dc.rights.robots | IndexNoFollow | en_US |
dc.subject.hlbsecondlevel | Materials Science and Engineering | en_US |
dc.subject.hlbsecondlevel | Chemistry | en_US |
dc.subject.hlbsecondlevel | Chemical Engineering | en_US |
dc.subject.hlbsecondlevel | Biological Chemistry | en_US |
dc.subject.hlbtoplevel | Engineering | en_US |
dc.subject.hlbtoplevel | Science | en_US |
dc.subject.hlbtoplevel | Health Sciences | en_US |
dc.description.peerreviewed | Peer Reviewed | en_US |
dc.contributor.affiliationum | Department of Chemistry, University of Michigan, Ann Arbor, Michigan, USA 48109-1055 | en_US |
dc.contributor.affiliationum | Department of Chemistry, University of Michigan, Ann Arbor, Michigan, USA 48109-1055 | en_US |
dc.description.bitstreamurl | http://deepblue.lib.umich.edu/bitstream/2027.42/31955/1/0000908.pdf | en_US |
dc.identifier.doi | http://dx.doi.org/10.1016/S0040-4020(01)89538-7 | en_US |
dc.identifier.source | Tetrahedron | en_US |
dc.owningcollname | Interdisciplinary and Peer-Reviewed |
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