000110579 001__ 110579
000110579 005__ 20230519145610.0
000110579 0247_ $$2doi$$a10.1002/ejoc.202100332
000110579 0248_ $$2sideral$$a127276
000110579 037__ $$aART-2021-127276
000110579 041__ $$aeng
000110579 100__ $$aRodriguez, S.
000110579 245__ $$aThe Pseudotransannular Ring Opening of 1-Aminocyclohept-4-ene-derived Epoxides in the Synthesis of Tropane Alkaloids: Total Synthesis of (±)-Ferrugine
000110579 260__ $$c2021
000110579 5060_ $$aAccess copy available to the general public$$fUnrestricted
000110579 5203_ $$aWe 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.
000110579 536__ $$9info:eu-repo/grantAgreement/ES/DGA/E34-20R$$9info:eu-repo/grantAgreement/ES/MCIU-FEDER-CTQ2017-83633P$$9info:eu-repo/grantAgreement/ES/MICINN/PID2019-104090RB-100
000110579 540__ $$9info:eu-repo/semantics/openAccess$$aby-nc-nd$$uhttp://creativecommons.org/licenses/by-nc-nd/3.0/es/
000110579 590__ $$a3.261$$b2021
000110579 592__ $$a0.738$$b2021
000110579 591__ $$aCHEMISTRY, ORGANIC$$b19 / 57 = 0.333$$c2021$$dQ2$$eT2
000110579 593__ $$aPhysical and Theoretical Chemistry$$c2021$$dQ2
000110579 593__ $$aOrganic Chemistry$$c2021$$dQ2
000110579 655_4 $$ainfo:eu-repo/semantics/article$$vinfo:eu-repo/semantics/publishedVersion
000110579 700__ $$aUria, U.
000110579 700__ $$aReyes, E.
000110579 700__ $$aPrieto, L.
000110579 700__ $$aRodríguez-Rodríguez, M.
000110579 700__ $$0(orcid)0000-0003-3433-6701$$aTejero, T.$$uUniversidad de Zaragoza
000110579 700__ $$0(orcid)0000-0002-2202-3460$$aMerino, P.$$uUniversidad de Zaragoza
000110579 700__ $$aVicario, J.L.
000110579 7102_ $$12013$$2765$$aUniversidad de Zaragoza$$bDpto. Química Orgánica$$cÁrea Química Orgánica
000110579 773__ $$g2021, 20 (2021), 2855-2861$$pEUR J ORG CHEM$$tEuropean Journal of Organic Chemistry$$x1434-193X
000110579 8564_ $$s2972432$$uhttps://zaguan.unizar.es/record/110579/files/texto_completo.pdf$$yVersión publicada
000110579 8564_ $$s2596930$$uhttps://zaguan.unizar.es/record/110579/files/texto_completo.jpg?subformat=icon$$xicon$$yVersión publicada
000110579 909CO $$ooai:zaguan.unizar.es:110579$$particulos$$pdriver
000110579 951__ $$a2023-05-18-16:07:46
000110579 980__ $$aARTICLE