Facile synthesis of (-)-ascochlorin using palladium-catalyzed three component coupling reaction

Makoto Aoki, Kenji Kawashima, Hirohisa Fujihara, Isao Shimizu

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Abstract

(-)-Ascochlorin was synthesized using palladium-catalyzed three component coupling reaction. Reaction of the aryl iodide 3, isoprene, and sodium p-toluenesulfinate in the presence of Pd2(dba)3CHCl 3 catalyst and NaHCO3 gave the 4-aryl-2-methyl-2- butenylsulfone 5 selectively in 68% yield. The allylic sulfone 5 was converted into the useful intermediate 2 in 5 steps, which was subjected to Julia olefination with the aldehyde 4 and deprotection gave (-)-ascochlorin.

Original languageEnglish
Pages (from-to)654-655
Number of pages2
JournalChemistry Letters
Volume36
Issue number5
DOIs
Publication statusPublished - 2007 May 5

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ASJC Scopus subject areas

  • Chemistry(all)

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