The Pseudotransannular Ring Opening of 1-Aminocyclohept-4-ene-derived Epoxides in the Synthesis of Tropane Alkaloids: Total Synthesis of (±)-Ferrugine
Rodriguez, S. ; Uria, U. ; Reyes, E. ; Prieto, L. ; Rodríguez-Rodríguez, M. ; Tejero, T. (Universidad de Zaragoza) ; Merino, P. (Universidad de Zaragoza) ; Vicario, J.L.
Resumen: We have optimized a synthetic approach to (±)-Ferrugine in 8 steps starting from 5-aminocyclohept-1-ene and using the Brønsted acid-catalyzed pseudotransannular ring-opening of the epoxide derived from this cycloheptene as the key step for the construction of the 8-azabicyclo[3.2.1]octane central core. While attempting the enantioselective synthesis of this natural product from enantiopure 2-hydroxy-8-azabicyclo[3.2.1]octane we have found that this compound shows a pronounced tendency to racemize via an achiral symmetric aziridinium intermediate. This racemization side process has been studied in detail using both experimental and computational methods.
Idioma: Inglés
DOI: 10.1002/ejoc.202100332
Año: 2021
Publicado en: European Journal of Organic Chemistry 2021, 20 (2021), 2855-2861
ISSN: 1434-193X
Factor impacto JCR: 3.261 (2021)
Categ. JCR: CHEMISTRY, ORGANIC rank: 19 / 57 = 0.333 (2021) - Q2 - T2
Factor impacto SCIMAGO: 0.738 - Physical and Theoretical Chemistry (Q2) - Organic Chemistry (Q2)
Financiación: info:eu-repo/grantAgreement/ES/DGA/E34-20R
Financiación: info:eu-repo/grantAgreement/ES/MCIU-FEDER-CTQ2017-83633P
Financiación: info:eu-repo/grantAgreement/ES/MICINN/PID2019-104090RB-100
Tipo y forma: Article (Published version)
Área (Departamento): Área Química Orgánica (Dpto. Química Orgánica)
You must give appropriate credit, provide a link to the license, and indicate if changes were made. You may do so in any reasonable manner, but not in any way that suggests the licensor endorses you or your use. You may not use the material for commercial purposes. If you remix, transform, or build upon the material, you may not distribute the modified material.
Exportado de SIDERAL (2023-05-18-16:07:46)
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Idioma: Inglés
DOI: 10.1002/ejoc.202100332
Año: 2021
Publicado en: European Journal of Organic Chemistry 2021, 20 (2021), 2855-2861
ISSN: 1434-193X
Factor impacto JCR: 3.261 (2021)
Categ. JCR: CHEMISTRY, ORGANIC rank: 19 / 57 = 0.333 (2021) - Q2 - T2
Factor impacto SCIMAGO: 0.738 - Physical and Theoretical Chemistry (Q2) - Organic Chemistry (Q2)
Financiación: info:eu-repo/grantAgreement/ES/DGA/E34-20R
Financiación: info:eu-repo/grantAgreement/ES/MCIU-FEDER-CTQ2017-83633P
Financiación: info:eu-repo/grantAgreement/ES/MICINN/PID2019-104090RB-100
Tipo y forma: Article (Published version)
Área (Departamento): Área Química Orgánica (Dpto. Química Orgánica)
You must give appropriate credit, provide a link to the license, and indicate if changes were made. You may do so in any reasonable manner, but not in any way that suggests the licensor endorses you or your use. You may not use the material for commercial purposes. If you remix, transform, or build upon the material, you may not distribute the modified material. Exportado de SIDERAL (2023-05-18-16:07:46)
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Record created 2022-02-10, last modified 2023-05-19