Efficient synthesis of a key intermediate of DV-7751 via optical resolution or microbial reduction.
Two efficient and practical methods of synthesis of the C-10 substituent of DV-7751 (1), a novel quinolone carboxylic acid, were established. The first method utilizes an optical resolution of racemic 8-amino-6-benzyl-6-azaspiro[3.4]octane (13), while the second employs an enantioselective microbial reduction of 6-benzyl-5,8-dioxo-6-azaspiro[3.4]octane (8b). The enantiomeric excess of (S)-8-amino-6-benzyl-6-azaspiro[3.4]octane (11) with each method of synthesis is greater than 96%.
Miyadera
A
A
Chemical Technology Research Laboratories, Daiichi Pharmaceutical Co., Ltd., Tokyo, Japan.
Satoh
K
K
Imura
A
A
D000890:Anti-Infective Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism; D001203:Ascomycota / Q000378:metabolism*; D002851:Chromatography, High Pressure Liquid; D024841:Fluoroquinolones; D008956:Models, Chemical; D013237:Stereoisomerism
D000890:Anti-Infective Agents; D024841:Fluoroquinolones; C084755:DV 7751a