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【结 构 式】 
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【药物名称】 【化学名称】6,6,9,13,15,16-Hexamethyl-14-hydroxy-2,8-dioxabicyclo[10.4.0]hexadeca-12,14,16-trien-7-one 【CA登记号】 【 分 子 式 】C20H30O4 【 分 子 量 】334.4597 |
【开发单位】Alfa Wassermann (Originator) 【药理作用】Angina pectoris, Treatment of, Atherosclerosis Therapy, CARDIOVASCULAR DRUGS, Lipoprotein Disorders, Treatment of , METABOLIC DRUGS, Treatment of Disorders of the Coronary Arteries and Atherosclerosis, Antioxidants |
合成路线1
Arylbutanone (I), which was in equilibrium with its hemiacetal cyclic form, was alkylated with isopropyl 5-bromo-2,2-dimethyl-pentanoate (II) in the presence of NaH to afford ether (III). After saponification of the isopropyl and acetate esters of (III) with ethanolic KOH, the resulting ketoacid (IV) was reduced with NaBH4 to yield hydroxyacid (V). Finally, cyclization of (V) using 2,2'-dipyridyl disulfide, triphenylphosphine and silver perchlorate produced the target macrocyclic lactone.
| 【1】 Baldazzi, C.; et al.; Medium sized lactones with hyplipidaemic and antio. Bioorg Med Chem 1999, 7, 2, 411. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 23819 | 4-hydroxy-2,3,6-trimethyl-5-(3-oxobutyl)phenyl acetate | C15H20O4 | 详情 | 详情 | |
| (II) | 23820 | isopropyl 5-bromo-2,2-dimethylpentanoate | C10H19BrO2 | 详情 | 详情 | |
| (III) | 23821 | isopropyl 5-[4-(acetoxy)-2,3,5-trimethyl-6-(3-oxobutyl)phenoxy]-2,2-dimethylpentanoate | C25H38O6 | 详情 | 详情 | |
| (IV) | 23822 | 5-[4-hydroxy-2,3,5-trimethyl-6-(3-oxobutyl)phenoxy]-2,2-dimethylpentanoic acid | C20H30O5 | 详情 | 详情 | |
| (V) | 23823 | 5-[4-hydroxy-2-(3-hydroxybutyl)-3,5,6-trimethylphenoxy]-2,2-dimethylpentanoic acid | C20H32O5 | 详情 | 详情 |