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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.

Synthesis of Sesquiterpene Alcohols such as Nerolidol and Farnesol by Cross Coupling Reactions of Ene-type Chlorides with Prenylmagnesium Chloride