Gephyrotoxin

Gephyrotoxin is a naturally occurring product that stems from the Colombian tropical frog Dendrobates histrionicus.

This alkaloid skin secretion was first isolated from the tropical frog in 1977 by Daly and his fellow workers.

Due to this demand and the scarcity and lack of abundance of the tree frog the synthesis of this product is of much interest.

[1] The first total synthesis of gephyrotoxin was performed by Kishi and his co-workers, here they prepped an intermediate from L-pyroglutamic acid in 18 steps.

Unlike others that included a poorly diastereoselective step, this process allowed for the development of two stereogenic centers at the same time.