Studies Directed Toward the Total Synthesis of Histrionicotoxin

Author: Cherpeck, Richard Eugene

Year: 1980

Degree: Dissertation (Ph.D.)

Advisor: Evans, David A.

Committee Member: Unknown, Unknown

Option: Chemistry

DOI: 10.7907/dh0c-9d30

Abstract

Histrionicotoxin (HTX) is a unique alkaloid secreted from the skin glands of the arrow poison frog, Dendrobates histrionicus. This base has been found to be a highly active venom as well as a mucosal tissue irritant toward both mammals and reptiles. Syntheses of perhydrohistrionicotoxin (H₁₂-HTX), which exhibits all of the biological activities that histrionicotoxin does, and a photoaffinity labeled derivative of H₁₂-HTX are described.

An approach to the synthesis of the cis-enyne moieties in HTX is presented. This method utilizes the stereoselective synthesis of β-hydroxy acid derivatives obtained via the boron enolates of 3-acyl-oxazolidine-2-ones.

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