(3aR,14bS)-2-methoxy-1,5,6,8,9,14b-hexahydro-4H-cyclopenta[a][1,3]dioxolo[4,5-h]pyrrolo[2,1-b][3]benzazepin-1-yl 2,6-dioxoheptanoate -Drug Synthesis Database

【结构式】

【分子编号】52798

【品名】(3aR,14bS)-2-methoxy-1,5,6,8,9,14b-hexahydro-4H-cyclopenta[a][1,3]dioxolo[4,5-h]pyrrolo[2,1-b][3]benzazepin-1-yl 2,6-dioxoheptanoate

【CA登记号】

【分子式】C₂₅H₂₉NO₇

【分子量】455.5078

【元素组成】C 65.92% H 6.42% N 3.07% O 24.59%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号：(IV)

The oxidation of 2-methyl-1-cyclopentene-1-carbaldehyde (I) with O3 and Ag2O gives 2,6-dioxoheptanoic acid (II), which is esterified with cephalotaxine (III) by means of (COCl)2, yielding the ester (IV). Reformatsky reaction of (IV) with methyl bromoacetate (V) and Zn affords the adduct (VI), which is treated with an excess of methylmagnesium iodide to provide the target homoharringtonine (as a single diastereomer), along with some starting cephalotaxine that is separated by chromatography.

参考文献中间体

合成目标

【1】 Hiranuma, S.; Hudlicky, T.; Synthesis of homoharringtonine and its derivative by partial esterification of cephalotaxine. Tetrahedron Lett 1982, 23, 34, 3431.
【2】 Hiranuma, S.; et al.; Studies in Cephalotaxus alkaloids. Stereospecific total synthesis of homoharringtonine. J Org Chem 1983, 48, 26, 5321.

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)	52795	2-methyl-1-cyclopentene-1-carbaldehyde		C₇H₁₀O	详情	详情
(II)	52796	2,6-dioxoheptanoic acid		C₇H₁₀O₄	详情	详情
(III)	52797	(3aS,14bS)-2-ethyl-1,5,6,8,9,14b-hexahydro-4H-cyclopenta[a][1,3]dioxolo[4,5-h]pyrrolo[2,1-b][3]benzazepin-1-ol		C₁₉H₂₃NO₃	详情	详情
(IV)	52798	(3aR,14bS)-2-methoxy-1,5,6,8,9,14b-hexahydro-4H-cyclopenta[a][1,3]dioxolo[4,5-h]pyrrolo[2,1-b][3]benzazepin-1-yl 2,6-dioxoheptanoate		C₂₅H₂₉NO₇	详情	详情
(V)	12309	methyl 2-bromoacetate; methyl bromoacetate	96-32-2	C₃H₅BrO₂	详情	详情
(VI)	52799	1-[(1S,3aR,14bS)-2-methoxy-1,5,6,8,9,14b-hexahydro-4H-cyclopenta[a][1,3]dioxolo[4,5-h]pyrrolo[2,1-b][3]benzazepin-1-yl] 4-methyl 2-hydroxy-2-(4-oxopentyl)succinate		C₂₈H₃₅NO₉	详情	详情

Extended Information