Stereoselective and Regiodivergent Allylic Suzuki-Miyaura Cross-Coupling of 2-Ethoxydihydropyranyl Boronates: Synthesis and Confirmation of Absolute Stereochemistry of Diospongin B.
Oxygen-containing heterocycles such as pyrans are a common substructure present in a variety of natural products and pharmaceutical drugs. Highly functionalized 4- and 6-aryl/heteroaryl dihydropyran derivatives are assembled by a highly stereoselective, ligand-controlled regiodivergent sp(3)-sp(2) Suzuki-Miyaura cross-coupling of a 2-ethoxy dihydropyranyl boronate derived from a catalytic enantioselective inverse-electron-demand oxa[4 + 2] cycloaddition. The scope and selectivity of this method were assessed along with an application to a concise total synthesis of the diarylheptanoid natural product diospongin B.
Department of Chemistry, Centennial Centre for Interdisciplinary Science, University of Alberta , Edmonton, Alberta T6G 2G2, Canada.
Taras
T
Rybak
Department of Chemistry, Centennial Centre for Interdisciplinary Science, University of Alberta , Edmonton, Alberta T6G 2G2, Canada.
Dennis G
DG
Hall
D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D001897:Boronic Acids / Q000737:chemistry*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D061565:Cycloaddition Reaction; D036381:Diarylheptanoids / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry
D001688:Biological Products; D001897:Boronic Acids; D036381:Diarylheptanoids; D011714:Pyrans; C521318:diospongin B; D010165:Palladium