1055263-44-9Relevant academic research and scientific papers
Enantioselective Synthesis of Tropanes: Br?nsted Acid Catalyzed Pseudotransannular Desymmetrization
Carrillo, Luisa,Merino, Pedro,Reyes, Efraim,Rodriguez, Sandra,Tejero, Tomás,Uria, Uxue,Vicario, Jose L.
, p. 6780 - 6784 (2020)
The enantioselective synthesis of tropanols has been accomplished through chiral phosphoric acid catalyzed pseudotransannular ring opening of 1-aminocyclohept-4-ene-derived epoxides. The reaction proceeds together with the desymmetrization of the starting
The Pseudotransannular Ring Opening of 1-Aminocyclohept-4-ene-derived Epoxides in the Synthesis of Tropane Alkaloids: Total Synthesis of (±)-Ferrugine
Merino, Pedro,Prieto, Liher,Reyes, Efraim,Rodríguez-Rodríguez, Marta,Rodriguez, Sandra,Tejero, Tomás,Uria, Uxue,Vicario, Jose L.
, p. 2855 - 2861 (2021)
We have optimized a synthetic approach to (±)-Ferrugine in 8 steps starting from 5-aminocyclohept-1-ene and using the Br?nsted 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.
A two-directional approach to the anatoxin alkaloids: Second synthesis of homoanatoxin and efficient synthesis of anatoxin-a
Roe, Stephen J.,Stockman, Robert A.
supporting information; experimental part, p. 3432 - 3434 (2009/02/05)
Total syntheses of the potent neurotoxins, environmental hazards, and biochemical probes anatoxin-a and homoanatoxin have been achieved from a common intermediate using a combined two-directional synthesis-tandem reaction strategy which includes key advan
