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

早稲田大学

研究成果: Article › 査読

1 被引用数 (Scopus)

抄録

(-)-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.

本文言語	English
ページ（範囲）	654-655
ページ数	2
ジャーナル	Chemistry Letters
巻	36
号	5
DOI	https://doi.org/10.1246/cl.2007.654
出版ステータス	Published - 2007 5 5

ASJC Scopus subject areas

Chemistry(all)

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10.1246/cl.2007.654

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引用スタイル

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AU - Aoki, Makoto

AU - Kawashima, Kenji

AU - Fujihara, Hirohisa

AU - Shimizu, Isao

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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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