A biomimetic synthesis of shimalactone A and B is described. Its key features are an unprecedented acid-catalyzed cyclization of a dienyl β-ketolactone and a Stille coupling/8π-6π electrocyclization cascade to create the oxabicyclo[2.2.1]heptane and bicyclo[4.2.0]octadiene, respectively. The synthesis is convergent and void of protecting groups.
ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Organic Chemistry