New Asymmetric Total Synthesis of (+)-Strychnine

New Asymmetric Total Synthesis of (+)-Strychnine

Author: ChemistryViews.org

Strychnine (pictured) is a complex molecule and a challenging target for total synthesis. Chemists continually try to find more concise paths to this toxic natural product.

Yong Qin and colleagues, Sichuan University, Chengdu, China, have developed a new synthesis strategy for a concise, catalytic, asymmetric total synthesis of (+)-strychnine. The team used an enantioselective Michael addition and two cascade reactions as key steps. The synthesis started from a known chiral aldehyde ester.

A photoinduced radical cascade reaction and a bioinspired cascade rearrangement were used to construct the molecule’s framework. The photocatalytic cascade reaction allowed the team to efficiently prepare a tetracyclic alkaloid intermediate, which was converted into the desired strychnine core using an oxidation-rearrangement sequence.


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