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Protecting-Group-Free Formal Synthesis of Aspidospermidine: Ring-Opening Cyclization of Spirocyclopropane with Amine Followed by Regioselective Alkylations

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posted on 2019-12-03, 20:43 authored by Hisanori Nambu, Takafumi Tamura, Takayuki Yakura
A concise formal synthesis of (±)-aspidospermidine via Stork’s intermediate, which could be used as a divergent synthesis of Aspidosperma alkaloids, was achieved by employing a ring-opening cyclization of spirocyclopropane with amine followed by a regioselective intramolecular/intermolecular alkylation sequence. Stork’s intermediate was synthesized in only six steps from a simple starting material, 1,3-cyclohexanedione, and was converted into (±)-aspidospermidine. To the best of our knowledge, this synthesis of Stork’s intermediate involves the least number of steps to date. Furthermore, no protecting groups were used during this synthesis.

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