Process for preparing adjacently disubstituted ketones, novel prostaglandins E1 and anti-thrombotic compositions containing them
申请人:TEIJIN LIMITED
公开号:EP0019475A2
公开(公告)日:1980-11-26
Novel 7-hydroxyprostaglandins E1, or stereoisomers thereof, or protected derivatives thereof, having the following formula:
wherein R3 represents H, CH3 or C2H5, R9 represents H or CH3, R10 and R are identical or different, and each represents H, tetrahydropyranyl or t-butyldimethylsilyl.
Also provided is a process for producing adjacently disubstituted ketones including the above novel compounds, which process comprises reacting an a, #-unsaturated carbonyl compound with a cuprous salt and an organolithium compound in an aprotic inert organic medium in the presence of trialkylphosphine, the amounts of said cuprous salt and said organolithium compound being substantially equimolar, and reacting the product with a protected acetal derivative of an organic carbonyl compound or an aldehyde in the presence of a Lewis acid if necessary followed by reacting the product with a proton donor.
具有下式的新型 7-羟基前列腺素 E1 或其立体异构体或其保护衍生物:
其中 R3 代表 H、CH3 或 C2H5,R9 代表 H 或 CH3,R10 和 R 相同或不同,且各自代表 H、四氢吡喃基或叔丁基二甲基硅基。
还提供了一种生产包括上述新型化合物在内的邻接二取代酮的工艺,该工艺包括在三 烷基膦存在下,在氩惰性有机介质中使 a,#-不饱和羰基化合物与亚铜盐和有机锂化合物 反应、所述亚铜盐和所述有机锂化合物的量基本等摩尔,必要时在路易斯酸存在下,使产物与有机羰基化合物或醛的受保护缩醛衍生物反应,然后使产物与质子供体反应。