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【结 构 式】 
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【分子编号】63153 【品名】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 【CA登记号】 |
【 分 子 式 】C38H50O8 【 分 子 量 】634.8102 【元素组成】C 71.9% H 7.94% O 20.16% |
合成路线1
该中间体在本合成路线中的序号：(LIX)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.
| 【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 | CAS号 | 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 |