title: Stereoselective, Ag-Catalyzed Cyclizations To Access Polysubstituted Pyran Ring Systems: Synthesis of C1-C12 Subunit of Madeirolide A.
abstract: The exploration into the scope of a silver-catalyzed cyclization (AgCC) of propargyl benzoates for accessing pyran ring systems has been reported. The impact of the degree of substitution, nature of the substitution on the carbon backbone/benzoate moiety, and stereochemistry has been evaluated. The application of this methodology to the synthesis of the C1-C12 southern fragment of madeirolide A is disclosed.
authors.affiliation: Department of Chemistry, Oregon State University , 153 Gilbert Hall, Corvallis, Oregon 97331, United States.
authors.forename: Kazuhiro
authors.initials: K
authors.lastname: Watanabe
authors.affiliation: Department of Chemistry, Oregon State University , 153 Gilbert Hall, Corvallis, Oregon 97331, United States.
authors.forename: Jinming
authors.initials: J
authors.lastname: Li
authors.affiliation: Department of Chemistry, Oregon State University , 153 Gilbert Hall, Corvallis, Oregon 97331, United States.
authors.forename: Nagarathanam
authors.initials: N
authors.lastname: Veerasamy
authors.affiliation: Department of Chemistry, Oregon State University , 153 Gilbert Hall, Corvallis, Oregon 97331, United States.
authors.forename: Ankan
authors.initials: A
authors.lastname: Ghosh
authors.affiliation: Department of Chemistry, Oregon State University , 153 Gilbert Hall, Corvallis, Oregon 97331, United States.
authors.forename: Rich G
authors.initials: RG
authors.lastname: Carter
mesh_terms: D001565:Benzoates / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010293:Pargyline / Q000737:chemistry*; D011714:Pyrans / Q000737:chemistry*; D012834:Silver / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D001565:Benzoates; D018942:Macrolides; D011714:Pyrans; C582264:madeirolide A; D012834:Silver; D010293:Pargyline