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【结 构 式】 
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【药物名称】Saussureamine D 【化学名称】(+)-1-[(3R,3aS,5aR,6R,9bS)-6-Hydroxy-5a,9-dimethyl-2-oxo-2,3,3a,4,5,5a,6,7,9a,9b-decahydronaphtho[1,2-b]furan-3-ylmethyl]pyrrolidine-2(S)-carboxylic acid 【CA登记号】148225-51-8 【 分 子 式 】C20H29NO5 【 分 子 量 】363.45783 |
【开发单位】Kuraray (Originator) 【药理作用】Antiulcer Drugs, GASTROINTESTINAL DRUGS |
合成路线1
The epoxidation of costunolide (I) (isolated from the dried roots of Chinese plant Saussurea lappa) with MCPBA followed by cyclization by means of BF3·Et2O gives a mixture of two furo-naphthalene derivatives that is separated by gel chromatography. The desired isomer (II) is finally condensed with L-proline (III) by means of Et3N in refluxing ethanol.
| 【1】 Matsuda, H.; et al.; Absolute stereostructures and syntheses of saussureamines A, B, C, D and E, amino acid-sesquiterpene conjugates with gastroprotective effect, from the roots of Saussurea lappa. Tetrahedron 2000, 56, 39, 7763. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (IIa) | 42365 | (3aS,5aR,6R,9aS,9bR)-6-hydroxy-5a,9-dimethyl-3-methylene-3a,4,5,5a,6,7,9a,9b-octahydronaphtho[1,2-b]furan-2(3H)-one | C15H20O3 | 详情 | 详情 | |
| (IIb) | 42366 | (3aS,5aR,6R,9aS,9bR)-6-hydroxy-5a-methyl-3,9-dimethylenedecahydronaphtho[1,2-b]furan-2(3H)-one | C15H20O3 | 详情 | 详情 | |
| (I) | 42284 | (3aS,11aR)-6,10-dimethyl-3-methylene-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-2(3H)-one | C15H20O2 | 详情 | 详情 | |
| (III) | 16731 | L-proline | 147-85-3 | C5H9NO2 | 详情 | 详情 |
Extended Information