New Asymmetric Total Synthesis of (+)-Strychnine

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  • Published: 30 December 2018
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA
  • Source / Publisher: Organic Letters/ACS Publications
  • Associated Societies: American Chemical Society (ACS), USA
thumbnail image: New Asymmetric Total Synthesis of (+)-Strychnine

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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