dc.contributor.author | García Domínguez, Patricia | |
dc.contributor.author | Lorenzo Fernández, Paula | |
dc.contributor.author | Álvarez Rodríguez, Maria Rosana | |
dc.contributor.author | Rodríguez de Lera, Ángel | |
dc.date.accessioned | 2022-10-27T10:17:46Z | |
dc.date.available | 2022-10-27T10:17:46Z | |
dc.date.issued | 2022-10-07 | |
dc.identifier.citation | The Journal of Organic Chemistry, 87(19): 12510-12527 (2022) | spa |
dc.identifier.issn | 00223263 | |
dc.identifier.issn | 15206904 | |
dc.identifier.uri | http://hdl.handle.net/11093/3975 | |
dc.description | Financiado para publicación en acceso aberto: Universidade de Vigo/CISUG | |
dc.description.abstract | The 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.sponsorship | Xunta de Galicia | Ref. ED-431G/02-FEDER | spa |
dc.description.sponsorship | Xunta de Galicia | Ref. GRC ED431C 2021/045 | spa |
dc.description.sponsorship | Ministerio de Economía | Ref. PID2019-107855RB-I00 | spa |
dc.language.iso | eng | spa |
dc.publisher | The Journal of Organic Chemistry | spa |
dc.relation | info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/PID2019-107855RB-I00/ES | |
dc.rights | Attribution 4.0 International | |
dc.rights.uri | https://creativecommons.org/licenses/by/4.0/ | |
dc.title | Total synthesis of the proposed structure of (−)-novofumigatamide, isomers thereof, and analogues. Part I | en |
dc.type | article | spa |
dc.rights.accessRights | openAccess | spa |
dc.identifier.doi | 10.1021/acs.joc.2c01227 | |
dc.identifier.editor | https://pubs.acs.org/doi/10.1021/acs.joc.2c01227 | spa |
dc.publisher.departamento | Química orgánica | spa |
dc.publisher.grupoinvestigacion | Química Orgánica 1 | spa |
dc.subject.unesco | 2306 Química Orgánica | spa |
dc.date.updated | 2022-10-26T09:09:44Z | |
dc.computerCitation | pub_title=The Journal of Organic Chemistry|volume=87|journal_number=19|start_pag=12510|end_pag=12527 | spa |