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

• Published in: Molecules (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
• Language: English
• Published: Basel MDPI AG 01.11.2023
• Subjects: Biological activity; Dopamine; Dyskinesia; epoxide; monoterpene; nucleophilic substitution; Prottremine; Reagents; Solvents; synthetic methods

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...