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• W3146036827 abstract "Abstract 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." @default.
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• W3146036827 date "2021-05-26" @default.
• W3146036827 modified "2023-10-17" @default.
• W3146036827 title "The Pseudotransannular Ring Opening of 1‐Aminocyclohept‐4‐ene‐derived Epoxides in the Synthesis of Tropane Alkaloids: Total Synthesis of (±)‐Ferrugine" @default.
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• W3146036827 doi "https://doi.org/10.1002/ejoc.202100332" @default.
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