title: Total synthesis of (+/-)-magnofargesin.
abstract: [reaction: see text] A convenient method for the preparation of 2,5-dihydrofurans by using the chemistry of alkynyl(phenyl)iodonium salts is reported. Treatment of 3-alkoxy-1-alkynyl(phenyl)iodonium triflates with sodium benzenesulfinate generates an alkylidenecarbene, which undergoes [1,5]-C-H insertion to form 2-substituted 4-benzenesulfonyl-2,5-dihydrofurans in reasonable yield. These cyclic vinyl sulfones are functionalized in such a way as to make them useful starting materials for the preparation of lignans. The application of this methodology to the first total synthesis of (+/-)-magnofargesin is disclosed.
authors.affiliation: Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607-7061, USA. wardropd@uic.edu
authors.forename: Duncan J
authors.initials: DJ
authors.lastname: Wardrop
authors.forename: Joseph
authors.initials: J
authors.lastname: Fritz
mesh_terms: D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D007202:Indicators and Reagents; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D005663:Furans; D007202:Indicators and Reagents; C520049:magnofargesin