Since their discovery and isolation from the poison dart frog, Dendrobates histrionicus, in the early 1970’s, the histrionicotoxins such as 285A (1), as well as the unnatural perhydrohistrionicotoxin (2) have provided a variety of synthetic approaches and total syntheses. The core of these molecules contains a 1-azaspirocyclic ring system. This poster will highlight our effort to synthesis the 1-azaspiro cycle core in 4 steps from cyclopentanone and establishing a formal synthesis of perhydrohistrionicotoxin (2).

A tandem semipinacol/Beckmann rearrangement for the formal synthesis of perhydrohistrionicotoxin

ACS Spring Meeting 2021

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