Studies directed toward the synthesis of aspidophytine: construction of its perhydroquinoline core

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dc.citation.epage10462en_US
dc.citation.issueNumber21en_US
dc.citation.spage10454en_US
dc.citation.volumeNumber81en_US
dc.contributor.authorTürkmen, Y. E.en_US
dc.contributor.authorGravel, M.en_US
dc.contributor.authorRawal, V. H.en_US
dc.date.accessioned2018-04-12T10:51:47Z
dc.date.available2018-04-12T10:51:47Z
dc.date.issued2016en_US
dc.departmentDepartment of Chemistryen_US
dc.departmentInstitute of Materials Science and Nanotechnology (UNAM)en_US
dc.description.abstractWe 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.identifier.doi10.1021/acs.joc.6b01574en_US
dc.identifier.eissn1520-6904
dc.identifier.issn0022-3263
dc.identifier.urihttp://hdl.handle.net/11693/36744
dc.language.isoEnglishen_US
dc.publisherAmerican Chemical Societyen_US
dc.relation.isversionofhttp://dx.doi.org/10.1021/acs.joc.6b01574en_US
dc.source.titleJournal of Organic Chemistryen_US
dc.subjectAddition reactionsen_US
dc.subjectCarbonen_US
dc.subjectEnantioselectivityen_US
dc.subjectIonic liquidsen_US
dc.subjectOlefinsen_US
dc.subjectX ray crystallographyen_US
dc.subjectAza-Michael reactionen_US
dc.subjectContiguous stereocentersen_US
dc.subjectDiels-Alder reactionen_US
dc.subjectEnantioselective Diels-Alder reactionsen_US
dc.subjectIntramolecular substitutionsen_US
dc.subjectQuaternary centersen_US
dc.subjectSynthetic sequenceen_US
dc.subjectX-ray crystallographic analysisen_US
dc.subjectChemical reactionsen_US
dc.titleStudies directed toward the synthesis of aspidophytine: construction of its perhydroquinoline coreen_US
dc.typeArticleen_US

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Department of Chemistry
Institute of Materials Science and Nanotechnology (UNAM)