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Formal Total Synthesis of (±)-Strictamine by [2,3]-Sigmatropic Stevens Rearrangements

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2017

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https://doi.org/10.1002/chem.201605361
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Chemistry - A European Journal. 2017, 23(16), pp. 3938-3949. ISSN 0947-6539. eISSN 1521-3765. Available under: doi: 10.1002/chem.201605361

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To date, more than 100 congeners of the akuammiline alkaloid family have been isolated. Their signature structural element is a methanoquinolizidine moiety, a cage-like scaffold structurally related to adamantane. The structural variations of the family members originate from oxidative processes that mostly trigger rearrangements of the methanoquinolizidine motif. The family of the akuammiline alkaloids is best represented by strictamine. It bears the least functionalized carbon skeleton of all family members without lacking the signature structural motifs. Herein, we report the formal synthesis of strictamine through a Stevens [2,3]-sigmatropic rearrangement as a key step and the synthetic pitfalls related with its synthesis.

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ISO 690ECKERMANN, Ruben, Michael BREUNIG, Tanja GAICH, 2017. Formal Total Synthesis of (±)-Strictamine by [2,3]-Sigmatropic Stevens Rearrangements. In: Chemistry - A European Journal. 2017, 23(16), pp. 3938-3949. ISSN 0947-6539. eISSN 1521-3765. Available under: doi: 10.1002/chem.201605361
BibTex
@article{Eckermann2017-02-22Forma-38069,
  year={2017},
  doi={10.1002/chem.201605361},
  title={Formal Total Synthesis of (±)-Strictamine by [2,3]-Sigmatropic Stevens Rearrangements},
  number={16},
  volume={23},
  issn={0947-6539},
  journal={Chemistry - A European Journal},
  pages={3938--3949},
  author={Eckermann, Ruben and Breunig, Michael and Gaich, Tanja}
}
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