Total Synthesis of (+)-Pumiliotoxin A

Keywords

(+)-pumiliotoxin A - dendrobatid alkaloid - Ireland–Claisen rearrangement - Parikh–Doering oxidation - Corey–Fuchs reaction - iodide-promoted aza-Prins reaction

Significance

Overman and co-workers report the total synthesis of ( + )-pumiliotoxin A. The alkaloid was isolated in 1967 from the skin of the Panamanian poison frog Dendrobates pumilio. The skin secretions of these frogs have been employed by the Noanamá and the Emberá Native American tribes to poison blow darts.

Comment

Alkyne E is coupled with proline-derived building block F through an aluminum-mediated epoxide opening. The octahydroindolizine motif is constructed through an iodide-promoted aza-Prins reaction. The synthesis was completed after a deiodination and Birch reduction sequence, thus giving access to ( + )-pumiliotoxin A.

Publication History

Article published online:
20 December 2024