title: Fremy's salt-mediated oxidative addition. A new approach in the total synthesis of naturally dipetalolactone and its immunomodulatory activity.
abstract: The structure of the natural dipyranocoumarin dipetalolactone has been confirmed by an unambiguous synthetic route from resorcinol. This sequence was initiated by a pyran ring formation step which introduced the 3-chloro-3-methylbut-1-yne moiety. Then, the expected product undergoes a Fremy's salt-meditated oxidative addition followed by ring closure to yield dipetalolactone. Dipetalolactone was also found to have immunological activity in a mouse carcinoma S180-bearing mice cell line.
authors.affiliation: Faculty of Specific Education, Zagazig University, Zagazig 44519, Egypt. y2selem@yahoo.com
authors.forename: Yasser
authors.initials: Y
authors.lastname: Selim
authors.forename: Nabil
authors.initials: N
authors.lastname: Ouf
authors.forename: Mohamed
authors.initials: M
authors.lastname: Sakran
mesh_terms: D000107:Acetylation; D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D045744:Cell Line, Tumor; D002867:Chromones / Q000138:chemical synthesis* / Q000494:pharmacology; D003602:Cytotoxicity, Immunologic / Q000187:drug effects; D004354:Drug Screening Assays, Antitumor; D005260:Female; D007155:Immunologic Factors / Q000138:chemical synthesis* / Q000494:pharmacology; D007694:Killer Cells, Natural / Q000187:drug effects / Q000276:immunology; D007928:Lethal Dose 50; D008297:Male; D051379:Mice; D008813:Mice, Inbred ICR; D009368:Neoplasm Transplantation; D009603:Nitroso Compounds / Q000737:chemistry*; D010084:Oxidation-Reduction; D047368:Tumor Burden / Q000187:drug effects
chemical_list: D000970:Antineoplastic Agents; D002867:Chromones; D007155:Immunologic Factors; D009603:Nitroso Compounds; C587030:dipetalolactone; C001259:Fremy's salt
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