Studies directed toward the synthesis of aspidophytine: construction of its perhydroquinoline core
dc.citation.epage | 10462 | en_US |
dc.citation.issueNumber | 21 | en_US |
dc.citation.spage | 10454 | en_US |
dc.citation.volumeNumber | 81 | en_US |
dc.contributor.author | Türkmen, Y. E. | en_US |
dc.contributor.author | Gravel, M. | en_US |
dc.contributor.author | Rawal, V. H. | en_US |
dc.date.accessioned | 2018-04-12T10:51:47Z | |
dc.date.available | 2018-04-12T10:51:47Z | |
dc.date.issued | 2016 | en_US |
dc.department | Department of Chemistry | en_US |
dc.department | Institute of Materials Science and Nanotechnology (UNAM) | en_US |
dc.description.abstract | We have developed an efficient route for the synthesis of the perhydroquinoline core of the indole alkaloid aspidophytine (2), starting from commercially available and inexpensive 3-acetylpyridine. This densely functionalized perhydroquinoline core displays four contiguous stereocenters including an all-carbon quaternary center. The synthetic sequence features a highly effective Diels-Alder reaction using a carbamate-substituted siloxy diene accompanied by a spontaneous intramolecular substitution of the newly formed 3°-alkyl bromide with a carbamate group. The installation of the electron-rich aniline moiety was accomplished via a TBSOTf-mediated intramolecular aza-Michael reaction, and the relative stereochemistry of the aza-Michael product (30) was confirmed by X-ray crystallographic analysis. Among the useful transformations that were developed through this study is a highly enantioselective Diels-Alder reaction of a versatile cyclic carbamate siloxy diene. | en_US |
dc.description.provenance | Made available in DSpace on 2018-04-12T10:51:47Z (GMT). No. of bitstreams: 1 bilkent-research-paper.pdf: 179475 bytes, checksum: ea0bedeb05ac9ccfb983c327e155f0c2 (MD5) Previous issue date: 2016 | en |
dc.identifier.doi | 10.1021/acs.joc.6b01574 | en_US |
dc.identifier.eissn | 1520-6904 | |
dc.identifier.issn | 0022-3263 | |
dc.identifier.uri | http://hdl.handle.net/11693/36744 | |
dc.language.iso | English | en_US |
dc.publisher | American Chemical Society | en_US |
dc.relation.isversionof | http://dx.doi.org/10.1021/acs.joc.6b01574 | en_US |
dc.source.title | Journal of Organic Chemistry | en_US |
dc.subject | Addition reactions | en_US |
dc.subject | Carbon | en_US |
dc.subject | Enantioselectivity | en_US |
dc.subject | Ionic liquids | en_US |
dc.subject | Olefins | en_US |
dc.subject | X ray crystallography | en_US |
dc.subject | Aza-Michael reaction | en_US |
dc.subject | Contiguous stereocenters | en_US |
dc.subject | Diels-Alder reaction | en_US |
dc.subject | Enantioselective Diels-Alder reactions | en_US |
dc.subject | Intramolecular substitutions | en_US |
dc.subject | Quaternary centers | en_US |
dc.subject | Synthetic sequence | en_US |
dc.subject | X-ray crystallographic analysis | en_US |
dc.subject | Chemical reactions | en_US |
dc.title | Studies directed toward the synthesis of aspidophytine: construction of its perhydroquinoline core | en_US |
dc.type | Article | en_US |
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