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

Organic & Biomolecular Chemistry Pub Date: 2011-08-11 DOI: 10.1039/C1OB05898C

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.

Graphical abstract: Synthesis and configuration of the nonadecenetriol isolated from seeds of Persea americana
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