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【结 构 式】

【药物名称】Saussureamine E

【化学名称】1-[(3R,3aS,5aR,6R,9bS)-6-Hydroxy-5a-methyl-9-methylene-2-oxoperhydronaphtho[1,2-b]furan-3-ylmethyl]pyrrolidine-2(S)-carboxylic acid

【CA登记号】148225-52-9

【 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