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The intramolecular cycloaddition of azides with [omega]-chloroalkenes. A facile route to (+/-)-swainsonine and other indolizidine alkaloids

dc.contributor.authorPearson, William H.en_US
dc.contributor.authorLin, Ko-Chungen_US
dc.date.accessioned2006-04-10T13:59:51Z
dc.date.available2006-04-10T13:59:51Z
dc.date.issued1990en_US
dc.identifier.citationPearson,, William H., Lin, Ko-Chung (1990)."The intramolecular cycloaddition of azides with [omega]-chloroalkenes. A facile route to (+/-)-swainsonine and other indolizidine alkaloids." Tetrahedron Letters 31(52): 7571-7574. <http://hdl.handle.net/2027.42/28969>en_US
dc.identifier.urihttp://www.sciencedirect.com/science/article/B6THS-4325SPF-41/2/24fef28a470b2cd3a55d2cb60b5f56acen_US
dc.identifier.urihttps://hdl.handle.net/2027.42/28969
dc.description.abstractA potentially general route to the 1-azabicyclo[n.m.O]alkane skeleton of various alkaloids is embodied in the intramolecular 1,3-dipolar cycloaddition of aliphatic azides with [omega]-chloroalkenes. Cycloaddition is followed by rearrangement and intramolecular N-alkylation, affording bicyclic iminium ions 1 in one operation. The application of this method to the synthesis of (+/-)-[delta]-coniceine 6, (1S,2R,8aR)-indolizidine-1,2-diol 13 and (-)-swainsonine 15 is described.en_US
dc.format.extent356642 bytes
dc.format.extent3118 bytes
dc.format.mimetypeapplication/pdf
dc.format.mimetypetext/plain
dc.language.isoen_US
dc.publisherElsevieren_US
dc.titleThe intramolecular cycloaddition of azides with [omega]-chloroalkenes. A facile route to (+/-)-swainsonine and other indolizidine alkaloidsen_US
dc.typeArticleen_US
dc.rights.robotsIndexNoFollowen_US
dc.subject.hlbsecondlevelMaterials Science and Engineeringen_US
dc.subject.hlbsecondlevelChemistryen_US
dc.subject.hlbsecondlevelChemical Engineeringen_US
dc.subject.hlbsecondlevelBiological Chemistryen_US
dc.subject.hlbtoplevelEngineeringen_US
dc.subject.hlbtoplevelScienceen_US
dc.subject.hlbtoplevelHealth Sciencesen_US
dc.description.peerreviewedPeer Revieweden_US
dc.contributor.affiliationumDepartment of Chemistry, The University of Michigan, Ann Arbor, Michigan 48109 U.S.A.en_US
dc.contributor.affiliationumDepartment of Chemistry, The University of Michigan, Ann Arbor, Michigan 48109 U.S.A.en_US
dc.description.bitstreamurlhttp://deepblue.lib.umich.edu/bitstream/2027.42/28969/1/0000806.pdfen_US
dc.identifier.doihttp://dx.doi.org/10.1016/S0040-4039(00)97301-5en_US
dc.identifier.sourceTetrahedron Lettersen_US
dc.owningcollnameInterdisciplinary and Peer-Reviewed


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