塩化プレニルのGrignard試薬とエン型塩素化物のクロスカップリング反応を利用したセスキテルペンアルコール類の合成
1992 年 41 巻 3 号 p. 207-213
詳細
1992 年 41 巻 3 号 p. 207-213
The ene-type chlorination of terpenyl alcohols such as linalool (1 a), geraniol (1 b), nerol (1 c) and citronellol (1 d) with hypochlorous acid gave allylic chlorides (2 a-d) in good yields.
These compounds (2 a-d) reacted with prenylmagnesium chloride in the presence of Cu (I) salt to give SN 2' type cross coupling products (4 a-d) and (5 a-d) including nerolidol and farnesol, with high regioselectivity as shown in Table-2. Prenyl isopulegol (6) was prepared the by ene-type chlorination of isopulegol (1 e), followed by cross coupling reaction of the resulting product with prenylmagnesium chloride, as shown in Fig.-2.
