Electrochemical oxidation of polycyclic cyclopropanes and camphene. Novel synthesis of exo-5, 5-dimethyl-6-methylenebicyclo [2.2. 1] heptan-2-ol (nojigiku alcohol)

…, Y Matsubara, I Nishiguchi, T Hirashima…

Index: Uchida, Toshikazu; Matsubara, Yoshiharu; Nishiguchi, Ikuzo; Hirashima, Tsuneaki; Ohnishi, Takashi; Kanehira, Koichi Journal of Organic Chemistry, 1990 , vol. 55, # 9 p. 2938 - 2943

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Citation Number: 8

Abstract

Anodic oxidation of tricyclene (la) in acetic acid containing triethylamine, followed by hydrolysis, provides a facile and efficient synthesis of ero-5, 5-dimethyl-6-methylenebicyclo [2.2. l] heptan-2-01 (2a), named'nojigiku alcohol", which was isolated from the essential oil of chrysanthemum japonese. Furthermore, a method for large-scale production of 2a starting from the readily available impure starting tricyclene (la) has been developed by ...