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■ Synthesis of Diketonic Intermediates for the Total Syntheses of Dihydrojasmone, cis-Jasmone and dl-Muscone Starting from 1,n-Di(1-methyl-1H-imidazol-2-yl)-1,n-alkanedione

Shunsaku Ohta, Satoshi Hayakawa, Yoshimi Tamai, Teruyuki Yuasa, and Masao Okamoto

*Kyoto Pharmaceutical University, Misasagi, Yamashina, Kyoto 607-8414, Japan

Abstract

2,15-Dihydroxy-2,15-di(1-methyl-1H-imidazol-2-yl) hexadecane (3) was obtained by treating 1,14-(1-methyl-1H-imidazol-2-yl)-1,14-tetradecadione (2b) with an excess of CH₃MgI, while 1,4-di (1-methyl-1H-imidazol-2-yl)-4-trimethylsilyloxy-2-pentanone (6; R¹ = TMS) was obtained by the similar treatment of 1,4-(1-methyl-1H-imidazol-2-yl)-1,4-butadione (2a) followed by trimethylsilylation. These products (3 and 6) were convertible into the known diketonic intermediates for the synthesis of dl-muscone, dihydrojasmone and cis-jasmone.