title: Total synthesis of acortatarin A using a Pd(II)-catalyzed spiroketalization strategy.
abstract: The total synthesis of acortatarin A relying on a Pd(II)-catalyzed spiroketalization is reported. This strategy allows a single stereocenter in the spiroketalization substrate to produce the target efficiently under mild conditions, installing the necessary oxygenation in the backbone through an allylic transposition. The synthesis also verifies that pollenopyrroside B and acortatarin A are the same compound, and electrochemical studies suggest that the reported bioactivity is not due to simple antioxidant properties.
authors.affiliation: Department of Chemistry, University of Florida, Gainesville, Florida 32611, United States.
authors.forename: Nicholas V
authors.initials: NV
authors.lastname: Borrero
authors.forename: Aaron
authors.initials: A
authors.lastname: Aponick
mesh_terms: D002384:Catalysis; D015394:Molecular Structure; D009025:Morpholines / Q000138:chemical synthesis* / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*; D013141:Spiro Compounds / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: D009025:Morpholines; D013141:Spiro Compounds; C550646:acortatarin A; D010165:Palladium