Abstract
The insect pheromone (2S,3S,7RS)-diprionyl acetate (1) was prepared from (S,S)-2,3-dimethylcyclohexanone (2), which in turn was obtained by the 1,4-addition of lithium dimethylcuprate to (S)-(+)-carvone (3) and diastereoselective protonation of the resulting enolate with phenyl salicylate, followed by removal of the isopropenyl group and hydrogenation. Baeyer−Villiger rearrangement of (S,S)-2 and opening of the lactone (S,S)-8 with octyllithium provided the hydroxy ketone (S,S)-9, which was transformed into the target molecule (2S,3S,7RS)-1 by carbonyl olefination with Petasis’ reagent, acylation and hydrogenation.
Sign-in/Register to access full text options 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
