Syntheses of All Four Stereoisomers of Pyriculol

Abstract

All four Stereoisomers of pyriculol were synthesized to assist in forming a correlation between their chemical structure and biological activity. The (R, E)-2-hydroxy-3-pentenal derivative was coupled with a lithium acetylide derivative to give a diastereomeric mixture of the acetylenic alcohol, which led to the antipode of pyriculol and its 3'-epimer. Similarly obtained were the natural pyriculol and its 3'-epimer from the (S)-isomer of this aldehyde.