Journal
CHEMICAL RECORD
Volume 15, Issue 5, Pages 872-885Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/tcr.201500024
Keywords
cascade reactions; natural products; reductive amination; samarium; strychnine
Categories
Funding
- Deutsche Forschungsgemeinschaft
- Fonds der Chemischen Industrie
- Studienstiftung des Deutschen Volkes
- Bayer HealthCare
Ask authors/readers for more resources
Strychnine stands out from the group of classical natural products as one of the first complex compounds to be isolated in pure form and an extreme challenge to be structurally characterized. It has played a central role in natural product total syntheses and the surge in the development of innovative synthetic methods for many decades. Recently, we have accomplished one of the shortest formal total syntheses of strychnine (in ten steps and 14% overall yield or even shorter in eight steps and 10% overall yield). The evolution of a productive synthetic strategy, as well as the synthetic challenges tackled, are described here in detail, including examples of related transformations. The successful synthetic strategy was inspired by the premise that the core structure could be derived from simple aromatic indole precursors by a reductive SmI2-induced ketyl-aryl coupling. Other key reactions included a diastereoselective reduction and a regioselective elimination protocol. Altogether one of the shortest syntheses of iso-strychnine and hence of strychnine was established.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available