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DOI: 10.1055/s-0037-1611130
Divergent Route to Gelsedine-Type Alkaloids
Publication History
Publication Date:
19 November 2018 (online)
![](https://www.thieme-connect.de/media/synfacts/201812/i_c063_s1_10-1055_s-0037-1611130.gif)
Significance
Gelsedine-type natural products have attracted considerable interest from the synthetic community owing to their interesting biological properties and complex architectures. Ma and co-workers have developed and executed an elegant synthetic route culminating in the preparation of four such alkaloids relying on an asymmetric Michael addition, tandem oxidation-aldol cyclization, and a pinacol rearrangement.
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Comment
Indole derivative B and enone E underwent conjugate addition to furnish F. Oxidation and aldol cyclization resulted in the formation of key structure G in a single pot. Cationic rearrangement of G provided the oxabicyclo[3.2.2]nonane skeleton present in all targets. (–)-Gelsedilam was synthesized from H in four steps. (–)-Gelsemoxonine, (–)-gelsenicine, and (–)-gelsedine were accessed via ethyl ketone J.
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![](https://www.thieme-connect.de/media/synfacts/201812/i_c063_s1_10-1055_s-0037-1611130.gif)