Synthesis of 5,5,6-Fused Tricyclic Lactones: Stereocontrol of Three Consecutive Stereocenters
Abstract
We report a new, highly diastereoselective method for the synthesis of strained 5,5,6-fused tricyclic γ-lactones via a palladium-catalyzed tandem Heck/Suzuki cross-coupling reaction, followed by epoxidation and lactone-forming epoxide opening. Using this sequence, we prepared tricyclic γ-lactones with three consecutive stereocenters from simple, readily available starting materials, including one derived from enantiomerically pure biomass-based levoglucosenone. Our method provides a stereocontrolled approach to complex scaffolds of potential relevance in synthetic and medicinal chemistry.
Fields of Study & Subjects
Asymmetric Synthesis and Catalysis
Catalytic Cross-Coupling Reactions
Organic Chemistry Synthesis Methods
Publication details
- Journal / source
- Organic Letters
- Volume
- 28
- Issue
- 3
- Pages
- 1031–1035
- Publication date
- 12 January 2026
- Language
- EN