Synthesis of 7-azabicyclo[2.2.1]heptanes by anionic cyclization
✍ Scribed by Iain Coldham; Joan-Carles Fernàndez; David J. Snowden
- Publisher
- Elsevier Science
- Year
- 1999
- Tongue
- French
- Weight
- 202 KB
- Volume
- 40
- Category
- Article
- ISSN
- 0040-4039
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## Abstract magnified image The bromination (CuBr~2~, AcOEt/CHCI~3~) plus Favorskii rearrangement (EtONa, EtOH) of __N__‐carbethoxytropinone (**4**), readily available from tropinone (**3**), affords mixtures of __exo__‐ and __endo__‐isomers of 2,7‐dicarbethoxy‐7‐azabicyclo[2.2.1]heptane (**1b**)
Epibatidine (1) is a recently discovered trace alkaloid found pyrrole (7) with ethynyl p-tolyl sulfone (6) and subsequent steps has been optimized. The crucial last step, the reductive in the skin of a Latin-American poisonous frog. Its remarkably high analgetic activity is accompanied by high cleav