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Química Nova

Print version ISSN 0100-4042On-line version ISSN 1678-7064

Abstract

SANTOS, Reginaldo B. dos et al. SYNTHESIS AND DETERMINATION OF THE RELATIVE STEREOCHEMISTRY OF A NEW EPOXIDE ALDEHYDE CYCLOPENTANE MONOTERPENOID. Quím. Nova [online]. 2015, vol.38, n.10, pp.1260-1264. ISSN 1678-7064.  https://doi.org/10.5935/0100-4042.20150151.

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.

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