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【结 构 式】

【分子编号】42365

【品名】(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

【CA登记号】

【 分 子 式 】C15H20O3

【 分 子 量 】248.322

【元素组成】C 72.55% H 8.12% O 19.33%

与该中间体有关的原料药合成路线共 2 条

合成路线1

该中间体在本合成路线中的序号:(IIa)

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

合成路线2

该中间体在本合成路线中的序号:(IIa)

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