SÍNTESE E DETERMINAÇÃO DA ESTEREOQUÍMICA RELATIVA DE UM NOVO EPÓXIDO ALDEÍDO CICLOPENTANO MONOTERPENÓIDE

Abstract

In this study, we report the preparation of a new tetra-substituted epoxide aldehyde cyclopentane, which acts as a starting material for the synthesis of plinol, from (R)-(+)-epoxy-limonene. The synthesis was performed in three steps and resulted in a good yield. The structural determination was performed by 1H and 13C NMR, and the relative stereochemistry was defined by nuclear Overhauser effect (NOE) experiments with computer calculations of molecular modeling, particularly with respect to indirect coupling constant calculations.

Keywords

• plinol
• limonene oxide
• cyclopentane
• monoterpenoid