Synthesis of Terpenoids such as Geraniol and Farnesol by Cross Coupling Reactions

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  • クロスカップリング反応によるテルペン化合物の合成
  • クロス カップリング ハンノウ ニ ヨル テルペン カゴウブツ ノ ゴウセイ

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Abstract

The ene-type chlorination of benzyl prenyl ether (1 a) and benzyl geranyl ether (1 b) with hypochlorous acid gave allylic chlorides (2) in good yields. Allylic chlorides (2) reacted with Grignard reagents such as isoamylmagnesium bromide (2 a) and n-butylmagnesium bromide (2 b) in the presence of CuCl to give γ-ross coupling products (5) and (6) in high regioselectivities. Reactions of allylic chlorides (2) with prenylmagnesium chloride (2 c) were subsequently conducted in the presence of CuI to obtain the cross coupling products (4), (5) and (6).

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