Synthesis of Methyl (-)-Shikimate From D-Lyxose |
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| Authors: | Kin-Ichi Tadano Yoshihide Ueno Youichi Limura Tetsuo Suami |
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| Institution: | Department of Applied Chemistry, Faculty of Science and Technology , Keio University , Hiyoshi, Kohoku-ku, Yokohama, 223, Japan |
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| Abstract: | Abstract Methyl (-)-shikimate (1), the methyl ester of naturally occurring (-)-shikimic acid, has been synthesized from D-lyxose. The key reaction in the synthesis was a one-step construction of the cyclohexane ring by simultaneous C-C bond formation of both terminal carbons of a D-lyxose derived synthon (7) with the methylene carbon of dimethyl malonate. The cyclization products (9) and (9′) were transformed to some derivatives of shikimic acid. |
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