【结 构 式】 |
【分子编号】52627 【品名】 【CA登记号】 |
【 分 子 式 】C15H12O4 【 分 子 量 】256.25788 【元素组成】C 70.31% H 4.72% O 24.97% |
合成路线1
该中间体在本合成路线中的序号:(VI)The esterification of the carboxylic acid (II) with 2-iodo-6-methoxyphenol (I) by means of EDC and DMAP in dichloromethane gives the corresponding ester (III), which is cyclized by means of a Pd catalyst and TlOAc in refluxing acetonitrile to yield the spiranic 1-benzopyranone (IV). The cleavage of the ethylene ketal group of (IV) with Ph3C-BF4 in dichloromethane affords the spiranic diketone (V), which is dehydrogenated with (Ph-SeO)2O in refluxing dichloromethane to provide the spiranic cyclohexadienone (VI). The reaction of dienone (VI) with methylamine resulted in a spontaneous Michael addition to give the N-methylamide (VII), which is cyclized with paraformaldehyde and TFA yielding the tetracyclic compound (VIII). The enantioselective reduction of the ketonic group of (VIII) with L-Selectride in THF affords the alcohol (IX), which is finally reduced with LiAlH4 providing the target galanthamine.
【1】 Guillou, C.; et al.; An efficient total synthesis of (±)-galanthamine. Angew Chem. Int Ed 2001, 40, 24, 4745. |
中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
---|---|---|---|---|---|---|
(I) | 52622 | 2-iodo-6-(methyloxy)phenol | C7H7IO2 | 详情 | 详情 | |
(II) | 52623 | 2-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)acetic acid | C10H14O4 | 详情 | 详情 | |
(III) | 52624 | 2-iodo-6-(methyloxy)phenyl 2-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)acetate | C17H19IO5 | 详情 | 详情 | |
(IV) | 52625 | C17H18O5 | 详情 | 详情 | ||
(V) | 52626 | C15H14O4 | 详情 | 详情 | ||
(VI) | 52627 | C15H12O4 | 详情 | 详情 | ||
(VII) | 52628 | N-methyl-2-[6-(methyloxy)-3-oxo-4,4a-dihydrodibenzo[b,d]furan-9(3H)-yl]acetamide | C16H17NO4 | 详情 | 详情 | |
(VIII) | 52629 | 11-methyl-3-(methyloxy)-11,12-dihydro-4aH-[1]benzofuro[3a,3,2-ef][2]benzazepine-6,10(5H,9H)-dione | C17H17NO4 | 详情 | 详情 | |
(IX) | 52630 | 6-hydroxy-11-methyl-3-(methyloxy)-5,6,11,12-tetrahydro-4aH-[1]benzofuro[3a,3,2-ef][2]benzazepin-10(9H)-one | C17H19NO4 | 详情 | 详情 |