8-ethyl-15-[(4-methyl-1-piperazinyl)methyl]-2,3,11,14-tetrahydro-12H-[1,4]dioxino[2,3-g]pyrano[3',4':6,7]indolizino[1,2-b]quinolin-12-one -Drug Synthesis Database

【结构式】

【分子编号】54901

【品名】8-ethyl-15-[(4-methyl-1-piperazinyl)methyl]-2,3,11,14-tetrahydro-12H-[1,4]dioxino[2,3-g]pyrano[3',4':6,7]indolizino[1,2-b]quinolin-12-one

【CA登记号】

【分子式】C₂₈H₃₀N₄O₄

【分子量】486.57076

【元素组成】C 69.12% H 6.21% N 11.51% O 13.15%

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：(XLIV)

In a further procedure, hydrolysis of the methoxy pyranopyridine (XXV) employing iodotrimethylsilane gave lactam (XLII). This was condensed with the (hydroxymethyl)quinoline (XVII) under Mitsunobu conditions to afford adduct (XLIII). The hexacyclic system (XLIV) was then obtained by intramolecular Heck condensation of (XLIII) using palladium acetate and triphenylphosphine. Asymmetric dihydroxylation of (XLIV) yielded the alpha-hydroxy lactol (XLV). Finally, Swern oxidation of lactol (XLV) furnished the title lactone.

参考文献中间体

合成目标

【1】 Fang, F.G.; Xie, S. (GlaxoSmithKline Inc.); Method for preparing camptothecin derivs.. WO 9716454 .

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(XVII)	54877	{7-iodo-9-[(4-methyl-1-piperazinyl)methyl]-2,3-dihydro[1,4]dioxino[2,3-g]quinolin-8-yl}methanol	C₁₈H₂₂IN₃O₃	详情	详情
(XXV)	54885	4-ethyl-1H-pyrano[3,4-c]pyridin-8-yl methyl ether; 4-ethyl-8-methoxy-1H-pyrano[3,4-c]pyridine	C₁₁H₁₃NO₂	详情	详情
(XLII)	54899	4-ethyl-1,7-dihydro-8H-pyrano[3,4-c]pyridin-8-one	C₁₀H₁₁NO₂	详情	详情
(XLIII)	54900	4-ethyl-7-({7-iodo-9-[(4-methyl-1-piperazinyl)methyl]-2,3-dihydro[1,4]dioxino[2,3-g]quinolin-8-yl}methyl)-1,7-dihydro-8H-pyrano[3,4-c]pyridin-8-one	C₂₈H₃₁IN₄O₄	详情	详情
(XLIV)	54901	8-ethyl-15-[(4-methyl-1-piperazinyl)methyl]-2,3,11,14-tetrahydro-12H-[1,4]dioxino[2,3-g]pyrano[3',4':6,7]indolizino[1,2-b]quinolin-12-one	C₂₈H₃₀N₄O₄	详情	详情
(XLV)	54902	(8S)-8-ethyl-8,9-dihydroxy-15-[(4-methyl-1-piperazinyl)methyl]-2,3,8,9,11,14-hexahydro-12H-[1,4]dioxino[2,3-g]pyrano[3',4':6,7]indolizino[1,2-b]quinolin-12-one	C₂₈H₃₂N₄O₆	详情	详情

Extended Information