期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 23, 期 16, 页码 3938-3949出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201605361
关键词
[2; 3]-sigmatropic rearrangement; alkaloids; diazo compounds; Stevens rearrangement; total synthesis
资金
- Fonds der Chemischen Industrie through a Liebigstipendium
- Alexander von Humboldt Foundation by the Sofja Kovalevskaja prize
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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