Total synthesis of (+/-)-magnofargesin.
[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.
Wardrop
Duncan J
DJ
Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607-7061, USA. wardropd@uic.edu
Fritz
Joseph
J
D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D007202:Indicators and Reagents; D015394:Molecular Structure; D013237:Stereoisomerism
D005663:Furans; D007202:Indicators and Reagents; C520049:magnofargesin