【结 构 式】 |
【分子编号】11396 【品名】(1S,2S,4R)-4-Methyl-2-(1-methyl-1-phenylethyl)cyclohexanol 【CA登记号】 |
【 分 子 式 】C16H24O 【 分 子 量 】232.36596 【元素组成】C 82.7% H 10.41% O 6.89% |
合成路线1
该中间体在本合成路线中的序号:(A)A synthesis for optically pure (-)-huperzine A, through modification of the previously reported synthesis of (±)-huperzine A, has been described: Intermediate methyl ester (XI) of this synthesis [Drugs Fut 1990, 15(6): 616] is transesterified with (-)-8-phenylmenthol (A) in refluxing benzene to give the optical ester (XIa), suitable for a stereocontrolled cyclization. The cyclization of (XIa) with 2-methylacrolein, as in the previous synthesis, yields the tricyclic compound (XIIa) [an analogue of the previously reported (XII), but with the adequate absolute configuration]. The following step is dehydration to (XIVa), in the same way as in the case of (XIV) of the previous synthesis. From here, the previously reported synthetic route is repeated, finally yielding optically pure (-)-huperzine A. In some steps, separation of undesirable minor amounts of other enantiomers must be performed.
【1】 Yamada, F.; Kozikowski, A.P.; Reddy, E.R.; Pang, Y.P.; Miller, J.H.; McKinney, M.; A route to optically pure (-)-huperzine-A - Molecular modeling and invitro pharmacology. J Am Chem Soc 1991, 113, 12, 4695. |
中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
---|---|---|---|---|---|---|
11387 | 2-Methylacrylaldehyde; Methacrylaldehyde | 78-85-3 | C4H6O | 详情 | 详情 | |
(A) | 11396 | (1S,2S,4R)-4-Methyl-2-(1-methyl-1-phenylethyl)cyclohexanol | C16H24O | 详情 | 详情 | |
(XIa) | 11397 | (1S,2S,4R)-4-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl 2-methoxy-6-oxo-5,6,7,8-tetrahydro-5-quinolinecarboxylate | C27H33NO4 | 详情 | 详情 | |
(XIIa) | 11398 | (1S,2S,4R)-4-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl (1S,9R)-10-hydroxy-5-methoxy-11-methyl-13-oxo-6-azatricyclo[7.3.1.0(2,7)]trideca-2,4,6-triene-1-carboxylate | C31H39NO5 | 详情 | 详情 | |
(XIVa) | 11399 | (1S,2S,4R)-4-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl (1S,9R)-5-methoxy-11-methyl-13-oxo-6-azatricyclo[7.3.1.0(2,7)]trideca-2,4,6,10-tetraene-1-carboxylate | C31H37NO4 | 详情 | 详情 | |
(XI) | 11386 | methyl 2-methoxy-6-oxo-5,6,7,8-tetrahydro-5-quinolinecarboxylate | C12H13NO4 | 详情 | 详情 |