Show simple item record

dc.contributor.authorGarcía Domínguez, Patricia
dc.contributor.authorLorenzo Fernández, Paula
dc.contributor.authorÁlvarez Rodríguez, Maria Rosana 
dc.contributor.authorRodríguez de Lera, Ángel 
dc.date.accessioned2022-10-27T10:17:46Z
dc.date.available2022-10-27T10:17:46Z
dc.date.issued2022-10-07
dc.identifier.citationThe Journal of Organic Chemistry, 87(19): 12510-12527 (2022)spa
dc.identifier.issn00223263
dc.identifier.issn15206904
dc.identifier.urihttp://hdl.handle.net/11093/3975
dc.descriptionFinanciado para publicación en acceso aberto: Universidade de Vigo/CISUG
dc.description.abstractThe total synthesis of the suggested structure of (−)-novofumigatamide, a natural product containing a C3-reverse prenylated N-acetyl-exo-hexahydropyrrolo[2,3-b]indole motif fused to a 10-membered ring lactam, was achieved using the macrolactam formation in advance of a diastereoselective bromocyclization and reverse prenylation steps. Since the NMR data of the synthetic sample did not match those of the natural product, the endo-bromo precursor of a N-Boc analogue and additional diastereomers derived from L-Trp were also synthesized. Five alternative synthetic routes, which differed in the order of final key steps used for the construction of the 10-membered ring lactam and the hexahydropyrrolo[2,3-b]indole framework within the polycyclic skeleton and also in the amide bond selected for the ring-closing of the macrolactam, were thoroughly explored. Much to our dismay, the lack of spectroscopic correlations between the proposed structure of natural (−)-novofumigatamide and the synthetic products suggested a different connectivity between the atoms. Additional synthetic efforts to assemble alternative structures of the natural product and isomers thereof (see accompanying paper; DOI: 10.1021/acs.joc.2c01228) further highlighted the frustrating endeavors toward the identification of a natural product.en
dc.description.sponsorshipXunta de Galicia | Ref. ED-431G/02-FEDERspa
dc.description.sponsorshipXunta de Galicia | Ref. GRC ED431C 2021/045spa
dc.description.sponsorshipMinisterio de Economía | Ref. PID2019-107855RB-I00spa
dc.language.isoengspa
dc.publisherThe Journal of Organic Chemistryspa
dc.relationinfo:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/PID2019-107855RB-I00/ES
dc.rightsAttribution 4.0 International
dc.rights.urihttps://creativecommons.org/licenses/by/4.0/
dc.titleTotal synthesis of the proposed structure of (−)-novofumigatamide, isomers thereof, and analogues. Part Ien
dc.typearticlespa
dc.rights.accessRightsopenAccessspa
dc.identifier.doi10.1021/acs.joc.2c01227
dc.identifier.editorhttps://pubs.acs.org/doi/10.1021/acs.joc.2c01227spa
dc.publisher.departamentoQuímica orgánicaspa
dc.publisher.grupoinvestigacionQuímica Orgánica 1spa
dc.subject.unesco2306 Química Orgánicaspa
dc.date.updated2022-10-26T09:09:44Z
dc.computerCitationpub_title=The Journal of Organic Chemistry|volume=87|journal_number=19|start_pag=12510|end_pag=12527spa


Files in this item

[PDF]

    Show simple item record

    Attribution 4.0 International
    Except where otherwise noted, this item's license is described as Attribution 4.0 International