Synthesis and stereochemical assignment of geraniol- and nerol-derived Cygerol enantiomers |
| |
Authors: | Anna A Sukhanova Ilya A Puchkin Andrei A Vasilev Sergei G Zlotin |
| |
Institution: | N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991 Moscow, Russian Federation |
| |
Abstract: | The enantiomers (up to 99% ee) of both geraniol- and nerol-derived 2-cyclohexyl-5,9-dimethyldeca-4,8-dienoic acid, the active ingredient of the wound healing medication Cygerol, were prepared via a low-temperature alkylation, basic hydrolysis, derivatization with (S)-4-benzyloxazolidin-2-one and chromatographic separation steps. The absolute configuration of stereocenters in the antipodes having an (E)- or (Z)-geometry of the internal double bond was determined based on characteristic 1H NMR signals of the corresponding (S)-4-benzyloxazolidin-2-one-derived imides and on conversion to the known diethyl (S)-2-cyclohexylsuccinate and (S)-2-cyclohexylbutane-1,4-diol with reported specific rotations. |
| |
Keywords: | Corresponding author Fax: +7 499 135 5328 |
本文献已被 ScienceDirect 等数据库收录! |
|