title: Isolation, structural assignment, and total synthesis of barmumycin.
abstract: Barmumycin was isolated from an extract of the marine actinomycete Streptomyces sp. BOSC-022A and found to be cytotoxic against various human tumor cell lines. On the basis of preliminary one- and two-dimensional (1)H and (13)C NMR spectra, the natural compound was initially assigned the structure of macrolactone-type compound 1, which was later prepared by two different routes. However, major spectroscopic differences between isolated barmumycin and 1 led to revision of the proposed structure as E-16. On the basis of the synthesis of this new compound, and subsequent spectroscopic comparison of it to an authentic sample of barmumycin, the structure of the natural compound was indeed confirmed as that of E-16.
authors.affiliation: Institute for Research in Biomedicine, Barcelona Science Park, University of Barcelona, Baldiri Reixac 10, E-08028 Barcelona, Spain.
authors.forename: Adriana
authors.initials: A
authors.lastname: Lorente
authors.forename: Daniel
authors.initials: D
authors.lastname: Pla
authors.forename: Librada M
authors.initials: LM
authors.lastname: Cañedo
authors.forename: Fernando
authors.initials: F
authors.lastname: Albericio
authors.forename: Mercedes
authors.initials: M
authors.lastname: Alvarez
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification*; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification*; D045744:Cell Line, Tumor / Q000737:chemistry*; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D011759:Pyrrolidines / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification*; D013302:Streptomyces / Q000737:chemistry*
chemical_list: D000970:Antineoplastic Agents; D001688:Biological Products; D007783:Lactones; D011759:Pyrrolidines; C556253:barmumycin