Synthesis of a Potent Antimalarial Amphilectene

2012/11/15 by Sergey V. Pronin, Ryan A. Shenvi · 4 citations
Chemistry · Medicine · #Synthesis and Catalytic Reactions #Malaria Research and Control #Asymmetric Synthesis and Catalysis

paper · doi:10.1021/ja310129b

openalex publication_date 2012/11/15 · openalex created_date 2025/10/10 · openalex updated_date 2026/06/25

Abstract

7-Isocyano-11(20),14-epiamphilectadiene, the most potent of antimalarial amphilectenes, is synthesized in seven steps from readily available materials. The synthesis is enabled by a new dendrimeric triene (Danishefsky [3]-dendralene) and a new method for stereo- and chemoselective isocyanation. This chemistry provides a useful entry into an underexplored yet promising family of antimalarial terpenoids.

Cited by

• Multicomponent Diene‐Transmissive Diels–Alder Sequences Featuring Aminodendralenes
• Synthesis and Diels–Alder Reactivity of Substituted [4]Dendralenes
• [5]Radialene
• Dendralene [wikipedia]

Related

• C−H Activation Enables a Concise Total Synthesis of Quinine and Analogues with Enhanced Antimalarial Activity
• Total Synthesis and Biological Investigation of (−)‐Artemisinin: The Antimalarial Activity of Artemisinin Is not Stereospecific
• Practical Synthesis of the Dendralene Family Reveals Alternation in Behavior
• Total Synthesis of Antimalarial Macrolide Strasseriolide A by Ni/Zr-Mediated Reductive Ketone Coupling
• A Concise Synthesis of (+)-Artemisinin