Biomimetic synthesis of the shimalactones.
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.
Sofiyev
Vladimir
V
Department of Chemistry, University of California Berkeley, Berkeley, California 94720-1460, USA.
Navarro
Gabriel
G
Trauner
Dirk
D
D002384:Catalysis; D032842:Emericella / Q000737:chemistry; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
D007783:Lactones; C525891:shimalactone A; C525892:shimalactone B