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Total synthesis of (±)-20S-hydroxy-1,2-dehydro-pseudoaspidospermidine via a C–H activation/transannular cyclization strategy

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2017

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https://doi.org/10.1039/c7cc02699d
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Chemical Communications : ChemComm. 2017, 53(54), pp. 7451-7453. ISSN 1359-7345. eISSN 1364-548X. Available under: doi: 10.1039/c7cc02699d

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A total synthesis to the pseudoaspidospermidine family via a C-H activation/transannular cyclization strategy has been accomplished. The applicability of this approach is showcased in the concise synthesis (ten steps) of (±)-20S-hydroxy-1,2-dehydro-pseudoaspidospermidine (4) starting from literature known compound 11. Via a joint synthetic sequence we were also able to address the related iboga alkaloid (±)-isovelbanamine (7) in nine steps. Key features of this synthesis are a transannular cyclization to generate the pseudoaspidospermidine skeleton (C-H activation) and a Witkop photocyclization reaction providing a 9-membered lactam. It is also worth mentioning that the joint synthetic sequence can be carried out on a multigram scale.

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ISO 690LEITNER, Christian, Tanja GAICH, 2017. Total synthesis of (±)-20S-hydroxy-1,2-dehydro-pseudoaspidospermidine via a C–H activation/transannular cyclization strategy. In: Chemical Communications : ChemComm. 2017, 53(54), pp. 7451-7453. ISSN 1359-7345. eISSN 1364-548X. Available under: doi: 10.1039/c7cc02699d
BibTex
@article{Leitner2017Total-39623,
  year={2017},
  doi={10.1039/c7cc02699d},
  title={Total synthesis of (±)-20S-hydroxy-1,2-dehydro-pseudoaspidospermidine via a C–H activation/transannular cyclization strategy},
  number={54},
  volume={53},
  issn={1359-7345},
  journal={Chemical Communications : ChemComm},
  pages={7451--7453},
  author={Leitner, Christian and Gaich, Tanja}
}
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