11-hydroxy-15-methyl-7-[3-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-1-({[4-(methyloxy)phenyl]methyl}oxy)-2-propenyl]-13-methylidene-6,21-dioxabicyclo[15.3.1]henicosa-3,9,19-trien-5-one -Drug Synthesis Database

【结构式】

【分子编号】63152

【品名】11-hydroxy-15-methyl-7-[3-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-1-({[4-(methyloxy)phenyl]methyl}oxy)-2-propenyl]-13-methylidene-6,21-dioxabicyclo[15.3.1]henicosa-3,9,19-trien-5-one

【CA登记号】

【分子式】C₃₈H₅₀O₇

【分子量】618.8108

【元素组成】C 73.76% H 8.14% O 18.1%

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：(LVIII)

The cyclization of the hydroxyacid (LV) by means of 2,4,6-trichlorobenzoyl chloride and TEA in THF/benzene gives the acetylenic macrolactone (LVI), which is reduced with Lindlar catalyst and 1-hexene in ethyl acetate to yield the cis-macrolactone (LVII). The Mom-protecting group of (LVII) is selectively removed by means of PPTS in tert-butanol to afford the allylic alcohol (LVIII), which is submitted to a Sharpless epoxidation with t-BuOOH, (+)-DET and Ti(OiPr)4 in dichloromethane providing the epoxide (LIX). Finally, the Pmb-protecting group of (LIX) is removed by means of DDQ in dichloromethane to furnish the target Laulimalide.

参考文献中间体

合成目标

【1】 Ghosh, A.K.; Wang, Y.; Kim, J.T.; Total synthesis of microtubule-stabilizing agent (-)-laulimalide. J Org Chem 2001, 66, 26, 8973.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(LV)	63149	4-((2R,6R)-6-{(2S,6S,7E,10S,11S,12E)-10-hydroxy-11-[(4-methoxybenzyl)oxy]-6-(methoxymethoxy)-2-methyl-13-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]-4-methylene-7,12-tridecadienyl}-5,6-dihydro-2H-pyran-2-yl)-2-butynoic acid	C₄₀H₅₄O₉	详情	详情
(LVI)	63150	15-methyl-7-[3-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-1-({[4-(methyloxy)phenyl]methyl}oxy)-2-propenyl]-13-methylidene-11-{[(methyloxy)methyl]oxy}-6,21-dioxabicyclo[15.3.1]henicosa-9,19-dien-3-yn-5-one	C₄₀H₅₂O₈	详情	详情
(LVII)	63151	15-methyl-7-[3-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-1-({[4-(methyloxy)phenyl]methyl}oxy)-2-propenyl]-13-methylidene-11-{[(methyloxy)methyl]oxy}-6,21-dioxabicyclo[15.3.1]henicosa-3,9,19-trien-5-one	C₄₀H₅₄O₈	详情	详情
(LVIII)	63152	11-hydroxy-15-methyl-7-[3-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-1-({[4-(methyloxy)phenyl]methyl}oxy)-2-propenyl]-13-methylidene-6,21-dioxabicyclo[15.3.1]henicosa-3,9,19-trien-5-one	C₃₈H₅₀O₇	详情	详情
(LIX)	63153	7-hydroxy-3-methyl-12-[3-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-1-({[4-(methyloxy)phenyl]methyl}oxy)-2-propenyl]-5-methylidene-9,13,22-trioxatricyclo[16.3.1.0~8,10~]docosa-15,19-dien-14-one	C₃₈H₅₀O₈	详情	详情

Extended Information