(+)-Stephadiamine is an unusual alkaloid isolated from the vine Stephania japonica. It features a norhasubanan skeleton, and contains two adjacent α-tertiary amines, which renders it an attractive synthetic target. Here, we present the first total synthesis of stephadiamine, which hinges on an efficient cascade reaction to implement the aza[4.3.3]propellane core of the alkaloid. The α-aminolactone moiety in a highly hindered position was installed via Tollens reaction and Curtius rearrangement. Useful building blocks for the asymmetric synthesis of morphine and (nor)hasubanan alkaloids are introduced.
CITATION STYLE
Hartrampf, N., Winter, N., Pupo, G., Stoltz, B. M., & Trauner, D. (2018). Total Synthesis of the Norhasubanan Alkaloid Stephadiamine. Journal of the American Chemical Society, 140(28), 8675–8680. https://doi.org/10.1021/jacs.8b01918
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