title: Cyclopropanations of olefin-containing natural products for simultaneous arming and structure activity studies.
abstract: Cyclopropanations of alkene-containing natural products that proceed under mild conditions are reported for simultaneous arming and structure-activity relationship studies. An alkynyl diazo ester under Rh(II) catalysis is employed for cyclopropanations of electron-rich olefins while an alkynyl sulfonium ylide is used for electron-poor olefins. This approach enables simultaneous natural product derivatization for SAR studies and arming (i.e., via alkyne attachment) for subsequent conjugation with reporter tags (e.g., biotin, fluorophores, photoaffinity labels) for mechanism of action studies including cellular target identification and proteome profiling experiments.
authors.affiliation: Department of Chemistry, Texas A&M University, P.O. Box 30012, College Station, Texas 77842-3012, United States.
authors.forename: Omar
authors.initials: O
authors.lastname: Robles
authors.forename: Sergio O
authors.initials: SO
authors.lastname: Serna-Saldívar
authors.forename: Janet A
authors.initials: JA
authors.lastname: Gutiérrez-Uribe
authors.forename: Daniel
authors.initials: D
authors.lastname: Romo
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D000480:Alkynes / Q000138:chemical synthesis* / Q000737:chemistry; D001688:Biological Products / Q000737:chemistry*; D002384:Catalysis; D003521:Cyclopropanes / Q000737:chemistry*; D004952:Esters; D007097:Imines; D015394:Molecular Structure; D029771:Rhodiola / Q000737:chemistry; D013329:Structure-Activity Relationship
chemical_list: D000475:Alkenes; D000480:Alkynes; D001688:Biological Products; D003521:Cyclopropanes; D004952:Esters; D007097:Imines