ZK-191784

Chemical Name: (1S,3R,5Z,7E,22E,24R)-24-[1-(5-Butyloxazol-2-yl)cyclopropyl]-9,10-secochola-5,7,10,22-tetraene-1,3,24-triol
CAS No. 198760-74-6
项目整合开发状态: Preclinical
项目研究机构: Schering AG (Originator)
合成路线:Coupling of 1-amino-2-hexanone (I) with 1-bromocyclopropanecarboxylic acid (II) produces keto amide (III).Subsequent cyclization of (III) under acidic conditions leads to oxazole (IV) .

合成路线:The 9,10-seco-steroid (V) is photochemically isomerized to (VI) under irradiation of a mercury lamp.Subsequent reduction of the methoxyamide function of (VI) employing DIBAL provides aldehyde (VII).Lithiation of the bromocyclopropane derivative (IV),followed by addition to aldehyde (VII) leads to carbinol (VIII) as a mixture of diastereoisomers.After chromatographic separation,the desired isomer is desilylated with tetrabutylammonium fluoride to furnish the title compound.