Total synthesis of (+/-)-magnofargesin |
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Authors: | Wardrop Duncan J Fritz Joseph |
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Affiliation: | Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607-7061, USA. wardropd@uic.edu |
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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. |
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