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Paper | Special issue | Vol 39, No. 2, 1994, pp.553-560
Published online, 1st January, 1970
DOI: 10.3987/COM-94-S(B)40
Lipase-catalyzed Resolution of Acetates of Racemic Phenolic Aporphines and Homoaporphines in Organic Solvent

Osamu Hoshino,* Hiroyuki Fuchino, and Masafumi Kikuchi

*Faculty of Pharmaceutical Sciences, Science University of Tokyo, 12, Ichigaya Funagawara-machi, Shinjuku-ku, Tokyo 162-0826, Japan

Abstract

Enzymatic resolution of (±)-1-acetoxy-2,9,10-trimethoxyaporphine (O-acetylthaliporphine)(3), (±)-2-acetoxy-1,9,10-trimethoxyaporphine (O-acetylpredicentrine)(4), and (±)-3-acetoxy-2,9,10-trimethoxyaporphines (5) by use of immobilized lipase in organic solvent gave resolved 3-5 and the corresponding hydroxyaporphines (9-11) in fair to good chemical and optical yields. Analogous reaction of (±)-1-acetoxy-2,10,11-trimethoxyhomoaporphine (6) did not take place, whereas that of (±)-2-acetoxy-1,10,11-trimethoxy- and (±)-3-acetoxy-2,10,11-trimethoxyhomoaporphines (7 and 8) produced optical active 7, 8 and hydroxyhomoaporphines (13, 14).