Synthesis and configuration of the nonadecenetriol isolated from seeds of Persea americana

Abstract

In an effort to establish the relative as well as absolute configuration of the trypanocidally active natural nonadec-6-en-1,2,4-triol isolated from Persea americana, the (2S,4R), (2S,4S), and (2R,4R) isomers were synthesized. The stereogenic centers taken from enantiopure chiral epoxy building blocks derived from inexpensive and readily available D-glucolactone. The (2R,4R) isomer gave ¹H and ¹³C NMR as well as specific rotation in excellent consistence with those reported for the natural triol.