title: Diastereoselective Michael-Claisen Cyclizations of γ-Oxa-α,β-unsaturated Ketones en Route to 5-Oxatetracyclines.
abstract: 5-Oxatetracyclines were synthesized from d-arabinose using sequential Michael-Claisen cyclization reactions via a 5-oxa-AB enone substrate. The 5-oxatetracyclines were found to have poor stability in aqueous buffer (pH 7.4, 37 °C) and showed little to no inhibition of bacterial growth (S. aureus, E. coli).
authors.affiliation: Department of Chemistry and Chemical Biology, Harvard University , Cambridge, Massachusetts 02138, United States.
authors.forename: Fan
authors.initials: F
authors.lastname: Liu
authors.affiliation: Department of Chemistry and Chemical Biology, Harvard University , Cambridge, Massachusetts 02138, United States.
authors.forename: Peter M
authors.initials: PM
authors.lastname: Wright
authors.affiliation: Department of Chemistry and Chemical Biology, Harvard University , Cambridge, Massachusetts 02138, United States.
authors.forename: Andrew G
authors.identifier: 0000-0001-9602-6915
authors.initials: AG
authors.lastname: Myers