Catalytic asymmetric synthesis of cannabinoids and menthol from neral.

ABSTRACT: The selective conversion of natural or synthetic neral to (1R,6S)-trans-isopiperitenol would enable and expedite sustainable routes to menthol^1,2 and cannabinoids^3-5. However, this reaction has been considered impossible because its product is more reactive to the required acid catalysts than its starting material, resulting in several side products^6-9. We now show that an unsymmetric, strong and confined chiral acid, a highly fluorinated imino-imidodiphosphate, catalyses this process with excellent efficiency and selectivity. Expanding the method to other α,β-unsaturated aldehydes could enable access to new cannabinoids and menthol derivatives not readily accessible previously. Mechanistic studies suggest that the confined catalyst accomplishes this reacti

SUBMITTER: Grimm JAA 

PROVIDER: S-EPMC10033408 | biostudies-literature | 2023 Mar

REPOSITORIES: biostudies-literature