【结 构 式】 |
【分子编号】48485 【品名】 【CA登记号】 |
【 分 子 式 】C48H55FeN2O5P 【 分 子 量 】826.793942 【元素组成】C 69.73% H 6.71% Fe 6.75% N 3.39% O 9.68% P 3.75% |
合成路线1
该中间体在本合成路线中的序号:(X)In an alternative procedure, aldehyde (II) was condensed with the indoloazepine (VIII) bearing a chiral N-alpha-ferrocenylethyl substituent to provide an equimolecular mixture of two separable C-20 epimeric diastereomers (IX) and (X), each accompanied by a minor diastereoisomeric byproduct. Cleavage of the ferrocenyl substituent with HOAc at 70 C provided the secondary amines (XI) and (XII). In this cleavage, the C-3,C-7 epimeric products were formed in 12% yield and were separated by chromatography. The major secondary amines (XI) and (XII) were N-benzylated to provide the corresponding tertiary amines (XIII). Reductive ring cleavage, followed by hydrogenolysis of the N-benzyl group, then gave the tricyclic compounds (VI), which were cyclized and rearranged as above.
【1】 Kuehne, M.E.; et al.; Enantioselective syntheses of coronaridine and 18-methoxycoronaridine. Tetrahedron 2001, 57, 11, 2085. |
中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
---|---|---|---|---|---|---|
(VIa) | 48480 | methyl (5R,7S)-5-[(2R)-2-(1,3-dioxolan-2-yl)-4-methoxybutyl]-1,2,3,4,5,6,7,8-octahydroazonino[5,4-b]indole-7-carboxylate | C24H34N2O5 | 详情 | 详情 | |
(VIb) | 48481 | methyl (5R,7S)-5-[(2S)-2-(1,3-dioxolan-2-yl)-4-methoxybutyl]-1,2,3,4,5,6,7,8-octahydroazonino[5,4-b]indole-7-carboxylate | C24H34N2O5 | 详情 | 详情 | |
(XIIIa) | 48488 | methyl (3aS,4R,11bR)-3-benzyl-4-[(2R)-2-(1,3-dioxolan-2-yl)-4-methoxybutyl]-2,3,3a,4,5,7-hexahydro-1H-pyrrolo[2,3-d]carbazole-6-carboxylate | C31H38N2O5 | 详情 | 详情 | |
(XIIIb) | 48489 | methyl (3aS,4R,11bR)-3-benzyl-4-[(2S)-2-(1,3-dioxolan-2-yl)-4-methoxybutyl]-2,3,3a,4,5,7-hexahydro-1H-pyrrolo[2,3-d]carbazole-6-carboxylate | C31H38N2O5 | 详情 | 详情 | |
(II) | 48474 | 4-(1,3-dioxolan-2-yl)-6-methoxyhexanal | C10H18O4 | 详情 | 详情 | |
(VIII) | 48483 | C38H39FeN2O2P | 详情 | 详情 | ||
(IX) | 48484 | C48H55FeN2O5P | 详情 | 详情 | ||
(X) | 48485 | C48H55FeN2O5P | 详情 | 详情 | ||
(XI) | 48486 | methyl (3aS,4R,11bR)-4-[(2R)-2-(1,3-dioxolan-2-yl)-4-methoxybutyl]-2,3,3a,4,5,7-hexahydro-1H-pyrrolo[2,3-d]carbazole-6-carboxylate | C24H32N2O5 | 详情 | 详情 | |
(XII) | 48487 | methyl (3aS,4R,11bR)-4-[(2S)-2-(1,3-dioxolan-2-yl)-4-methoxybutyl]-2,3,3a,4,5,7-hexahydro-1H-pyrrolo[2,3-d]carbazole-6-carboxylate | C24H32N2O5 | 详情 | 详情 |