Synthesis of the ABC Core of Daphniphyllum Alkaloids with a [5–6–7] Azatricyclic Scaffold via Ring Expansion of Azabicyclic and Azatricyclic Building Blocks
Clàudia Marquès,
David González-Lizana,
Faïza Diaba
et al.
Abstract:The [5–6–7] azatricyclic ABC core, found
in several Daphniphyllum alkaloids, has been synthesized
through a
novel route involving ring expansion of a perhydroindolone to afford
the AC ring system and a radical B ring closure as key steps. The
level of functionalization of the reported octahydro-1,7-ethanocyclohepta[b]pyrroles suggests that they can serve as valuable building
blocks in this alkaloid field. Also reported is the first synthesis
of homomorphans by the ring enlargement of 2-azabicyclo[3.3.1]nona… Show more
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