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【结 构 式】 
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【药物名称】 【化学名称】(-)-Acetic acid (3R,4S,6S,9aS)-4-methyl-6-[1(E),3(E)-octadienyl]perhydroquinolizin-3-yl ester 【CA登记号】 【 分 子 式 】C20H33NO2 【 分 子 量 】319.49151 |
【开发单位】 【药理作用】 |
合成路线1
The condensation of (3R,4S,6S,9aS)-3-(methoxymethoxy)-4-methyl-6-(phenylsulfonylmethyl)perhydroquinolizine (I) with trans-2-heptenal, followed by a treatment wit Na/Hg gives the 1,3-octadienyl-perhydroquinolizine (II), which is deprotected with HCl in refluxing methanol yielding the alcohol (III). Finally this compound is acetylated with acetic anhydride and pyridine to afford the target (-)-pictamine.
| 【1】 Toyooka, N.; Nemoto, H.; Application of chiral building blocks to the synthesis of drugs. Drugs Fut 2002, 27, 2, 143. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| 65170 | (E)-2-heptenal | 18829-55-5 | C7H12O | 详情 | 详情 | |
| (I) | 51726 | [(4S,6S,7R,9aS)-7-(methoxymethoxy)-6-methyloctahydro-2H-quinolizin-4-yl]methyl phenyl sulfone; (3R,4S,6S,9aS)-3-(methoxymethoxy)-4-methyl-6-[(phenylsulfonyl)methyl]octahydro-2H-quinolizine | C19H29NO4S | 详情 | 详情 | |
| (II) | 51727 | (3R,4S,6S,9aS)-3-(methoxymethoxy)-4-methyl-6-[(1E,3E)-1,3-octadienyl]octahydro-2H-quinolizine; (3R,4S,6S,9aS)-4-methyl-6-[(1E,3E)-1,3-octadienyl]octahydro-2H-quinolizin-3-yl methoxymethyl ether | C20H35NO2 | 详情 | 详情 | |
| (III) | 51728 | (3R,4S,6S,9aS)-4-methyl-6-[(1E,3E)-1,3-octadienyl]octahydro-2H-quinolizin-3-ol | C18H31NO | 详情 | 详情 |
Extended Information