title: Spiroacetal formation through telescoped cycloaddition and carbon-hydrogen bond functionalization: total synthesis of bistramide A.
abstract: Spiroacetals can be formed through a one-pot sequence of a hetero-Diels-Alder reaction, an oxidative carbon-hydrogen bond cleavage, and an acid treatment. This convergent approach expedites access to a complex molecular subunit which is present in numerous biologically active structures. The utility of the protocol is demonstrated through its application to a brief synthesis of the actin-binding cytotoxin bistramide A.
authors.affiliation: Department of Chemistry, University of Pittsburgh, Pittsburgh, PA 15260 (USA).
authors.forename: Xun
authors.initials: X
authors.lastname: Han
authors.forename: Paul E
authors.initials: PE
authors.lastname: Floreancig
mesh_terms: D000080:Acetals / Q000138:chemical synthesis / Q000737:chemistry*; D000081:Acetamides / Q000138:chemical synthesis / Q000737:chemistry*; D002244:Carbon / Q000737:chemistry; D061565:Cycloaddition Reaction; D006859:Hydrogen / Q000737:chemistry; D010084:Oxidation-Reduction; D011714:Pyrans / Q000138:chemical synthesis / Q000737:chemistry*; D013141:Spiro Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000080:Acetals; D000081:Acetamides; D011714:Pyrans; D013141:Spiro Compounds; C059975:bistratene A; D002244:Carbon; D006859:Hydrogen
keywords: CH activation; cycloaddition; natural products; spiro compounds; stereoselectivity