Total Syntheses of Alanenses A, B, and Lacinilene E
Abstract
-phthalimido-oxy isobutyrate (NPIB)-mediated deoxygenative C-C bond formation. Key improvements to McCormick's route to (±)-lacinilene C7-methyl ether enabled scalable access to common intermediates, while a streamlined de novo approach further enhanced the efficiency of the synthetic route. Importantly, a late-stage sequence of reductions, 9-I-9-BBN-mediated bis-demethylation, and DDQ oxidation overcame the previously encountered demethylation challenges to furnish the first synthetic sample of lacinilene E. This work demonstrates a convergent approach to cadinane sesquiterpenoids and showcases the versatility of NPIB-based chemistry.
Fields of Study & Subjects
Organic Chemistry Synthesis Methods
Advanced Synthetic Organic Chemistry
Biological Activity of Diterpenoids and Biflavonoids
Publication details
- Journal / source
- The Journal of Organic Chemistry
- Volume
- 91
- Issue
- 4
- Pages
- 1627–1633
- Publication date
- 9 January 2026
- Language
- EN