title: RCM-based synthesis of a variety of beta-C-glycosides and their in vitro anti-solid tumor activity.
abstract: The synthesis of a number of biologically relevant C-glycosides has been carried out through the use of an esterification-ring-closing metathesis (RCM) strategy. The required acid precursors were readily prepared via a number of standard chemical transformations followed by dehydrative coupling of these acids with several olefin alcohols 1 to yield the precursor esters 3 in excellent yield. Methylenation of the esters 3 was followed by RCM and in situ hydroboration-oxidation of the formed glycals to furnish the protected beta-C-glycosides 6 in good overall yield. Several examples were converted to the corresponding C-glycoglycerolipids 17 and subsequently screened against solid-tumor cell lines for in vitro differential cytotoxicity.
authors.affiliation: Department of Chemistry, Wayne State University, Detroit, MI 48202, USA. mpostem1@hfhs.org
authors.forename: Maarten H D
authors.initials: MH
authors.lastname: Postema
authors.forename: Jared L
authors.initials: JL
authors.lastname: Piper
authors.forename: Russell L
authors.initials: RL
authors.lastname: Betts
authors.forename: Frederick A
authors.initials: FA
authors.lastname: Valeriote
authors.forename: Halina
authors.initials: H
authors.lastname: Pietraszkewicz
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D045744:Cell Line, Tumor; D003500:Cyclization; D004354:Drug Screening Assays, Antitumor; D004951:Esterification; D006017:Glycolipids / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D006801:Humans
chemical_list: D000970:Antineoplastic Agents; D006017:Glycolipids; D006027:Glycosides; C015903:glycerolglycolipids