Taisho Pharmaceutical Co., Ltd.

Hiroaki Kamiyama

Nobuyuki Suzuki

Takashi Adachi

Takaaki Ishii

Masato Kashimura

Joji Sasaki

Takeshi Kuwada

Mitsuaki Hirotsuka

Motoko Oshida

Production of a bicyclo[3.1.0]hexane derivative, useful as a metabotropic glutamate receptor modulator, becomes possible by a production method that includes converting a compound represented by Formula (II) into a compound represented by Formula (III) by reaction with an acyl group donor in the presence of a microorganism-derived enzyme, without using an expensive optically active trans hydroxy ester as a starting material and without employing a fluorination reaction requiring an ultralow temperature reaction. Furthermore, since asymmetric synthesis can be carried out in a stage closer to the final product, the production method is useful as a production method that can mass produce a bicyclo[3.1.0]hexane derivative. 

Method of producing bicyclo[3.1.0] hexane derivative using enzyme

There is provided a preparation process useful for an efficient synthesis of 6-O-substituted ketolide derivatives by combining a characterized step of introduction of a substituent at the 6-position by selective cleavage of a C&mdash;O bond of the cyclic acetal at the 9-position side via 6,9-cyclic acetal 5-O-desosaminyl erythronolide derivative, a step of conversion into carbonyl groups at the 9- and 3-positions, and a step of 11,12-cyclic carbamation to lead to 6-O-substituted ketolide derivatives.

Process for producing erythromycin derivative

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Tokyo, Japan

Hiroaki Kamiyama