A New Stereoselective Approach to the Substitution of Allyl Hydroxy Group in para-Mentha-1,2-diol in the Search for New Antiparkinsonian Agents

Two approaches to the synthesis of para-menthene epoxide ((1S,5S,6R)-4) are developed. The first approach includes a reaction between chlorohydrin 7 and NaH in THF. The second involves the formation of epoxide in the reaction of corresponding diacetate 6 with sodium tert-butoxide. One possible mecha...

Full description

Saved in:
Bibliographic Details
Published inMolecules (Basel, Switzerland) Vol. 28; no. 21; p. 7303
Main Authors Podturkina, Alexandra V., Ardashov, Oleg V., Volcho, Konstantin P., Salakhutdinov, Nariman F.
Format Journal Article
LanguageEnglish
Published Basel MDPI AG 01.11.2023
Subjects
Biological activity
Dopamine
Dyskinesia
epoxide
monoterpene
nucleophilic substitution
Prottremine
Reagents
Solvents
synthetic methods
Online AccessGet full text

Cover

More Information
Summary:Two approaches to the synthesis of para-menthene epoxide ((1S,5S,6R)-4) are developed. The first approach includes a reaction between chlorohydrin 7 and NaH in THF. The second involves the formation of epoxide in the reaction of corresponding diacetate 6 with sodium tert-butoxide. One possible mechanism of this reaction is proposed to explain unexpected outcomes in the regio- and stereospecificity of epoxide (1S,5S,6R)-4 formation. The epoxide ring in (1S,5S,6R)-4 is then opened by various S- and O-nucleophiles. This series of reactions allows for the stereoselective synthesis of diverse derivatives of the monoterpenoid Prottremine 1, a compound known for its antiparkinsonian activity, including promising antiparkinsonian properties.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 14
content type line 23
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules28217303