A sulfone-based strategy for the preparation of 2,4-disubstituted furan derivatives |
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Authors: | Haines Nathan R VanZanten Aaron N Cuneo Anthony A Miller John R Andrews William J Carlson David A Harrington Ryan M Kiefer Adam M Mason Jeremy D Pigza Julie A Murphree S Shaun |
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Institution: | Department of Chemistry, Allegheny College, Meadville, Pennsylvania 16335, United States. |
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Abstract: | 2,4-Disubstituted furans are prepared by treating 2,3-dibromo-1-phenylsulfonyl-1-propene (DBP, 2) with 1,3-diketones under basic conditions. The furan-forming step involves a deacetylation, and the selectivity of this process depends upon the steric demand of the R group. The substituent in position 4 is elaborated by reaction of sulfonyl carbanions with alkyl halides, acyl halides, and aldehydes. Oxidative or reductive desulfonylation produces the 2,4-disubstituted furans in 60-92% yield. This strategy has been used to prepare rabdoketone A (12) and the naturally occurring nematotoxic furoic acid 13. |
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