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Design and Synthesis of Haptens for Application to the Preparation of Chiral 1,4-Dihydropyridines.

1998; Pharmaceutical Society of Japan; Volume: 46; Issue: 3 Linguagem: Inglês

10.1248/cpb.46.518

1347-5223

Kiyoshi Ikeda, Tatsuhisa Kato, Takehisa Suzuki, Kazuo Achiwa,

Synthetic Organic Chemistry Methods

Lipase-catalyzed enzymatic hydrolysis of dimethyl esters of 1, 4-dihydropyridines to the monoester, which is an important intermediate for the synthesis of optically active 1, 4-dihydropyridines, does not proceed directly. This paper describes the design and synthesis of novel haptens having a phosphonate group containing the requisite oxyanionic character to mimic the tetrahedral intermediate of hydrolysis, and the application of these compounds for generating antibodies with catalytic ability for the enantioselective partial hydrolysis of the dicarboxylic dimethyl ester (1) of a 1, 4-dihydropyridine derivative to generate the monocarboxylic acid (2).