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Paper | Regular issue | Vol 43, No. 5, 1996, pp.1031-1047
Published online, 1st January, 1970
DOI: 10.3987/COM-96-7421
Asymmetric Synthesis of Benzylic Quaternary Carbon Center via an Enzymatic Reaction

Shunsaku Shiotani,* Hirohiko Okada, Kumiko Nakamata, Takako Yamamoto, and Fumie Sekino

*Department of Chemistry, Faculty of Science, Toyama University, Gofuku 3190, Toyama 930, Japan


(R)-(+)-((R)-(+)-12) and (S)-(-)-1-formyl-1-methyl-7-methoxy-1,2,3,4-tetrahydronaphthalene ((S)-(-)-12) were synthesized based on enantioselective PLE hydrolysis of diethyl 2-(m-methoxyphenyl)-2-methylmalonate. From (R)-(+)-12, (+)-O-Methylaphanorphine (16) and (-)-aphanorphine were synthesized. (S)-(+)-1-(N-Acetyl-N-methylaminoethyl)-1-methyl-7-methoxytetralin (25) was synthesized from (S)-(-)-12. This transformation constitutes a formal synthesis of (-)-eptazocine.