title: Biomimetic synthesis of the shimalactones.
abstract: A biomimetic synthesis of shimalactone A and B is described. Its key features are an unprecedented acid-catalyzed cyclization of a dienyl beta-ketolactone and a Stille coupling/8pi-6pi 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.
authors: Department of Chemistry, University of California Berkeley, Berkeley, California 94720-1460, USA.
authors: Vladimir
authors: V
authors: Sofiyev
authors: Gabriel
authors: G
authors: Navarro
authors: Dirk
authors: D
authors: Trauner
mesh_terms: D002384:Catalysis; D032842:Emericella / Q000737:chemistry; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D007783:Lactones; C525891:shimalactone A; C525892:shimalactone B