title: A sulfone-based strategy for the preparation of 2,4-disubstituted furan derivatives.
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.
authors.affiliation: Department of Chemistry, Allegheny College, Meadville, Pennsylvania 16335, United States.
authors.forename: Nathan R
authors.initials: NR
authors.lastname: Haines
authors.forename: Aaron N
authors.initials: AN
authors.lastname: VanZanten
authors.forename: Anthony A
authors.initials: AA
authors.lastname: Cuneo
authors.forename: John R
authors.initials: JR
authors.lastname: Miller
authors.forename: William J
authors.initials: WJ
authors.lastname: Andrews
authors.forename: David A
authors.initials: DA
authors.lastname: Carlson
authors.forename: Ryan M
authors.initials: RM
authors.lastname: Harrington
authors.forename: Adam M
authors.initials: AM
authors.lastname: Kiefer
authors.forename: Jeremy D
authors.initials: JD
authors.lastname: Mason
authors.forename: Julie A
authors.initials: JA
authors.lastname: Pigza
authors.forename: S Shaun
authors.initials: SS
authors.lastname: Murphree