Total Syntheses of (+)-Penicibilaenes A and B via Enantioselective Desymmetrization
Abstract
Stereocontrolled total syntheses of (+)-penicibilaenes A and B were accomplished through three key steps: (1) Pd-catalyzed enantioselective desymmetrization to afford a pivotal chiral intermediate having an all-carbon quaternary stereogenic center, (2) ring-closing metathesis to form the bicyclo[3.3.1]nonane core, and (3) intramolecular nitrile oxide [3 + 2] cycloaddition to assemble the tricyclo[6.3.1.0 1,5 ]dodecane skeleton. Enantioselective desymmetrization delivered a highly functionalized cyclohexene, which provided access to (+)-penicibilaenes A and B.
Fields of Study & Subjects
Synthetic Organic Chemistry Methods
Marine Toxins and Detection Methods
Cyclopropane Reaction Mechanisms
Publication details
- Journal / source
- Organic Letters
- Publisher
- American Chemical Society (ACS)
- Volume
- 28
- Issue
- 4
- Pages
- 1452–1456
- Publication date
- 19 January 2026
- Language
- EN