C(1)-substituted (-)-menthone derivatives 3 were prepared by the stereoselective addition of the alkenyllithium reagents 9 to menthone (8) and subsequent acid catalyzed hydrolysis of the dioxolane protecting groups. Conjugate addition of cuprate reagents to enones 3a,b followed by a methanol quench directly gave the β-alkylcycloalkanones 7 via retro-aldol reactions in 80-91% ee.
All Science Journal Classification (ASJC) codes
- Drug Discovery
- Organic Chemistry