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

Makoto Aoki; Kenji Kawashima; Hirohisa Fujihara; Isao Shimizu

doi:10.1246/cl.2007.654

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

Makoto Aoki, Kenji Kawashima, Hirohisa Fujihara, Isao Shimizu^*

^*Corresponding author for this work

Waseda University

Research output: Contribution to journal › Article › peer-review

1 Citation (Scopus)

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 language	English
Pages (from-to)	654-655
Number of pages	2
Journal	Chemistry Letters
Volume	36
Issue number	5
DOIs	https://doi.org/10.1246/cl.2007.654
Publication status	Published - 2007 May 5

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Chemistry(all)

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title = "Facile synthesis of (-)-ascochlorin using palladium-catalyzed three component coupling reaction",

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.",

author = "Makoto Aoki and Kenji Kawashima and Hirohisa Fujihara and Isao Shimizu",

year = "2007",

month = may,

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doi = "10.1246/cl.2007.654",

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pages = "654--655",

journal = "Chemistry Letters",

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T1 - Facile synthesis of (-)-ascochlorin using palladium-catalyzed three component coupling reaction

AU - Aoki, Makoto

AU - Kawashima, Kenji

AU - Fujihara, Hirohisa

AU - Shimizu, Isao

PY - 2007/5/5

Y1 - 2007/5/5

N2 - (-)-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.

AB - (-)-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.

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DO - 10.1246/cl.2007.654

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EP - 655

JO - Chemistry Letters

JF - Chemistry Letters

IS - 5

ER -

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

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