| (-)-（3S, 6R）-3, 6-羟基-10-甲基十一酸及其三聚体的全合成 |
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| 引用本文： | 张宪恕,达世俊,焦阳,李惠芝,谢志翔,李瀛. (-)-（3S, 6R）-3, 6-羟基-10-甲基十一酸及其三聚体的全合成[J]. 中国化学, 2008, 26(7): 1315-1322. DOI: 10.1002/cjoc.200890239 |
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| 作者姓名： | 张宪恕 达世俊 焦阳 李惠芝 谢志翔 李瀛 |
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| 作者单位： | 兰州大学化学化工学院 兰州730000 |
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| 摘 要： | 以廉价易得的异戊基溴为起始原料，以烯丙基二异松莰烷基硼烷参与的不对称烯丙基化反应和Yamaguchi酯化反应为关键步骤，实现了对(-)-(3S,6R)-3,6-二羟基-10-甲基十一酸(总收率27.5％)及其三聚体(总收率24.5％)的不对称全合成。
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| 关 键 词： | 全合成、不对称烯丙基化、Yamaguchi酯化 |
| 收稿时间： | 2007-07-23 |
| 修稿时间： | 2008-02-20 |
Total Synthesis of (−)‐(3S,6R)‐3,6‐Dihydroxy‐10‐methylundecanoic Acid and Its Trimer |
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| Xian‐Shu ZHANG,Shi‐Jun DA,Yang JIAO,Hui‐Zhi LI,Zhi‐Xiang XIE,Ying LI. Total Synthesis of (−)‐(3S,6R)‐3,6‐Dihydroxy‐10‐methylundecanoic Acid and Its Trimer[J]. Chinese Journal of Chemistry, 2008, 26(7): 1315-1322. DOI: 10.1002/cjoc.200890239 |
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| Authors: | Xian‐Shu ZHANG Shi‐Jun DA Yang JIAO Hui‐Zhi LI Zhi‐Xiang XIE Ying LI |
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| Affiliation: | 1. State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, Gansu 730000, China;2. Tel.: 0086‐0931‐8913103;3. Fax: 0086‐0931‐8913103 |
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| Abstract: | The asymmetric total synthesis of (3S,6R)‐3,6‐dihydroxy‐10‐methylundecanoic acid and its trimer was accomplished from commercially available 1‐bromo‐3‐methylbutane in 11 steps in a 27.5% overall yield and 14 steps in a 24.5% overall yield, respectively. The key steps were asymmetric allylboration via allyldiisopinocampheylborane and Yamaguchi's esterification reaction. |
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| Keywords: | total synthesis asymmetric allylboration Yamaguchi reaction |
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