title: Phosphate Tether-Mediated Ring-Closing Metathesis for the Generation of P-Stereogenic, Z-Configured Bicyclo[7.3.1]- and Bicyclo[8.3.1]phosphates.
abstract: A phosphate tether-mediated ring-closing metathesis (RCM) study to the synthesis of Z-configured, P-stereogenic bicyclo[7.3.1]- and bicyclo[8.3.1]phosphates is reported. Investigations suggest that C3-substitution, olefin substitution, and proximity of the forming olefin to the bridgehead carbon of the bicyclic affect the efficiency and stereochemical outcome of the RCM event. This study demonstrates the utility of phosphate tether-mediated desymmetrization of C2-symmetric, 1,3-anti-diol-containing dienes in the generation of macrocyclic phosphates with potential synthetic and biological utility.
authors.affiliation: Department of Chemistry, University of Kansas , 1251 Wescoe Hall Drive, Lawrence, Kansas 66045-7582, United States.
authors.forename: Jana L
authors.initials: JL
authors.lastname: Markley
authors.affiliation: Department of Chemistry, University of Kansas , 1251 Wescoe Hall Drive, Lawrence, Kansas 66045-7582, United States.
authors.forename: Soma
authors.initials: S
authors.lastname: Maitra
authors.affiliation: Department of Chemistry, University of Kansas , 1251 Wescoe Hall Drive, Lawrence, Kansas 66045-7582, United States.
authors.forename: Paul R
authors.initials: PR
authors.lastname: Hanson
mesh_terms: D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis* / Q000737:chemistry*; D002384:Catalysis; D047028:Macrocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D010710:Phosphates / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D019086:Bridged Bicyclo Compounds, Heterocyclic; D047028:Macrocyclic Compounds; D010710:Phosphates