title: Synthesis of pluraflavin A "aglycone".
abstract: The "aglycone" of pluraflavin A (2) has been synthesized. The key features of this synthesis include a 1,3-dipolar cycloaddition between a nitrile oxide (cf. 14) and an olefin (22) to yield an isoxazoline followed by subsequent conversion into the gamma-pyrone of pluraflavin A. The epoxide moiety linked to the pyrone is installed prior to Diels-Alder installation of the D ring, which allows access to a number of potentially active cytotoxic intermediates en route to the final compound. The preliminary in vitro results of two such compounds are also included with the racemic title compound exhibiting cytotoxicity in the nanomolar range.
authors.affiliation: Department of Chemistry, Columbia University, Havemeyer Hall, 3000 Broadway, New York, New York 10027, USA.
authors.forename: Benjamin J D
authors.initials: BJ
authors.lastname: Wright
authors.forename: John
authors.initials: J
authors.lastname: Hartung
authors.forename: Feng
authors.initials: F
authors.lastname: Peng
authors.forename: Ryan
authors.initials: R
authors.lastname: Van de Water
authors.forename: Haibo
authors.initials: H
authors.lastname: Liu
authors.forename: Quen-Hui
authors.initials: QH
authors.lastname: Tan
authors.forename: Ting-Chao
authors.initials: TC
authors.lastname: Chou
authors.forename: Samuel J
authors.initials: SJ
authors.lastname: Danishefsky
mesh_terms: D000880:Anthraquinones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D004317:Doxorubicin / Q000737:chemistry; D006801:Humans
chemical_list: D000880:Anthraquinones; C440630:pluraflavin A; D004317:Doxorubicin