Total synthesis of 9-isocyanopupukeanane and 2-isocyanoallopupukeanane

9-Isocyanopupukeanane and 2-Isocyanoallopupukeanane belong to the class of isocyanoterpenes that have shown to exert promising antimalarial activity against blood- as well as liver-stage malaria parasite. An asymmetric synthesis of both natural products starting from the cheap and natural chiral building block carvone is envisioned. Key-step of the synthesis is a Pd-mediated cyclobutanol opening followed by a intramolecular Heck-type insertion for the construction of the bicyclic cores. SmI2-mediated coupling and a intramolecular aldol condensation would provide the tricycles of 9-isocyanopupukeanane and 2-isocyanoallopupukeanane. Functional group manipulations would provide the final molecules in a short and efficient way.

Project details

Drug-based Strategies

Jan 2017 — May 2018

$80,718

Switzerland