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.
Original language | English |
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Pages (from-to) | 1834-1841 |
Number of pages | 8 |
Journal | Tetrahedron Asymmetry |
Volume | 28 |
Issue number | 12 |
DOIs | |
Publication status | Published - 15 Dec 2017 |
Externally published | Yes |
Funding
This research was supported by the Russian Science Foundation (project no. 14-50-00126). A
All Science Journal Classification (ASJC) codes
- Catalysis
- Physical and Theoretical Chemistry
- Organic Chemistry
- Inorganic Chemistry