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Updated: May 22, 2025

A Direct, Early Stage Guanidinylation Protocol for the Synthesis of Complex Aminoguanidine-containing Natural Products
Published on: September 9, 2016
Concise Total Synthesis of Ambiguine P
Yifan Fei1,2, Bo Fan1, Zhigang Liu2,3
1Henan Institute of Advanced Technology and College of Chemistry, Zhengzhou University, Zhengzhou 450001, China.
None:
Ambiguine P (5) is a synthetically challenging representative of the hapalindole-type natural products. Inspired by the biosynthesis of this indole terpenoid family, we developed a Cope/Prins/Friedel-Crafts cascade, achieving a six-step synthesis of 5 from 2,2-dimethylcycloheptanone. Altered from the biosynthetic pathway, this cascade strategically commenced with a tricyclic indolenine derivative bearing a seven-membered ring, enabling efficient construction of the pentacyclic scaffold of 5. The oxidation state was elevated through chlorination and hydroxylation in the final stage.
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