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

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

Journal

Tetrahedron: Asymmetry
ISSN: 1362-511X , E-ISSN: 0957-4166

Output data

Year: 2017, Volume: 28, Number: 12, Pages: 1834-1841 Pages count : 8 DOI: 10.1016/j.tetasy.2017.10.024

Authors

Sukhanova Anna A. ¹ , Puchkin Ilya A. ¹ , Vasil'ev Andrei A. ¹ , Zlotin Sergei G. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991 Moscow, Russian Federation

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.

Sukhanova A.A. , Puchkin I.A. , Vasil'ev A.A. , Zlotin S.G.
Synthesis and stereochemical assignment of geraniol- and nerol-derived Cygerol enantiomers
Tetrahedron: Asymmetry. 2017. V.28. N12. P.1834-1841. DOI: 10.1016/j.tetasy.2017.10.024 OpenAlex

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W2768223950

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