Published in

Wiley, European Journal of Organic Chemistry, 20(2021), p. 2855-2861, 2021

DOI: 10.1002/ejoc.202100332

Links

Tools

Export citation

Search in Google Scholar

The Pseudotransannular Ring Opening of 1‐Aminocyclohept‐4‐ene‐derived Epoxides in the Synthesis of Tropane Alkaloids: Total Synthesis of (±)‐Ferrugine

Journal article published in 2021 by Sandra Rodriguez, Uxue Uria ORCID, Efraim Reyes ORCID, Liher Prieto ORCID, Marta Rodríguez‐Rodríguez ORCID, Tomás Tejero ORCID, Pedro Merino ORCID, Jose L. Vicario ORCID
This paper was not found in any repository, but could be made available legally by the author.
This paper was not found in any repository, but could be made available legally by the author.

Full text: Unavailable

Green circle
Preprint: archiving allowed
Upload
Orange circle
Postprint: archiving restricted
Upload
Red circle
Published version: archiving forbidden
Policy details
Data provided by SHERPA/RoMEO

Abstract

AbstractWe 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.