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J Org Chem. 2011 Oct 7;76(19):8131-7. doi: 10.1021/jo201529s. Epub 2011 Sep 1.

A sulfone-based strategy for the preparation of 2,4-disubstituted furan derivatives.

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1
Department of Chemistry, Allegheny College, Meadville, Pennsylvania 16335, United States.

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.

PMID:
21854041
DOI:
10.1021/jo201529s
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