Tetrahedron Letters

A stereoselective synthesis of (E)-1-halo-6, 6-dimethyl-2-hepten-4-yne: a key intermediate for terbinafine

SY Chou, CL Tseng, SF Chen

Index: Chou, Shan-Yen; Tseng, Chin-Lu; Chen, Shyh-Fong Tetrahedron Letters, 2000 , vol. 41, # 20 p. 3895 - 3898

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Citation Number: 6

Abstract

A study of the stereoselective halogenation of 6, 6-dimethyl-1-hepten-4-yn-3-ol (1) using a series of halogenating agents is described. Of the many agents investigated, boron trichloride is the most successful reagent for stereoselective halogenation (E: Z= 9: 1max). The resulting (E)-1-halo-6, 6-dimethyl-2-hepten-4-yne (2), a key intermediate for terbinafine, an antifungal agent, is obtained in good yield and stereoselectivity. Two structurally ...