Synthesis and stereochemical assignment of geraniol- and nerol-derived Cygerol enantiomers

Anna A. Sukhanova, Ilya A. Puchkin, Andrei A. Vasil'ev, Sergei G. Zlotin*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

1 Citation (Scopus)

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 languageEnglish
Pages (from-to)1834-1841
Number of pages8
JournalTetrahedron Asymmetry
Volume28
Issue number12
DOIs
Publication statusPublished - 15 Dec 2017
Externally publishedYes

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

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