| (8R,8aS)-及(8R,8aR)-8-羟基-5-吲哚里西啶酮的不对称合成:两个有用的羟基吲哚里西啶合成砌块 |
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| 引用本文： | 张洪奎,李欣,黄璜,黄培强.(8R,8aS)-及(8R,8aR)-8-羟基-5-吲哚里西啶酮的不对称合成:两个有用的羟基吲哚里西啶合成砌块[J].中国科学:化学,2011(4). |
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| 作者姓名： | 张洪奎 李欣 黄璜 黄培强 |
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| 作者单位： | 福建省化学生物学重点实验室厦门大学化学化工学院化学系; |
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| 基金项目： | 国家自然科学基金(20672089,20832005); 国家基础科学人才培养基金(J1030415); 国家重点基础研究发展计划(973项目,2010CB833200)的资助 |
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| 摘 要： | 以3-苄氧基哌啶-2,6-二酮衍生物20为起始原料,分别合成了两类新的合成砌块(8R,8aS)-及(8R,8aR)-8-羟基-5-吲哚里西啶酮19a/19b和15a/15b.19a/19b的合成是基于反式非对映立体选择性还原烷基化反应(dr=93:7),接着经4步转化而成;而化合物15a/15b的制备则以双烯29的RCM反应为关键步骤,再经顺式立体选择性催化氢化(dr=91:9)反应完成.此外,还原化合物15a得到了(8R,8aR)-8-羟基-5-吲哚里西啶18.
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| 关 键 词： | 吲哚里西啶 合成砌块 非对映选择性合成 RCM反应 催化氢化 |
Asymmetric syntheses of (8R,8aS)-and (8R,8aR)-8-hydroxy-5-indolizidinones:Two promising oxygenated indolizidine building blocks |
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| ZHANG HongKui,LI Xin,HUANG Huang & HUANG PeiQiang Key Laboratory for Chemical Biology of Fujian Province.Asymmetric syntheses of (8R,8aS)-and (8R,8aR)-8-hydroxy-5-indolizidinones:Two promising oxygenated indolizidine building blocks[J].Scientia Sinica Chimica,2011(4). |
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| Authors: | ZHANG HongKui LI Xin HUANG Huang & HUANG PeiQiang Key Laboratory for Chemical Biology of Fujian Province |
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| Institution: | ZHANG HongKui,LI Xin,HUANG Huang & HUANG PeiQiang Key Laboratory for Chemical Biology of Fujian Province,Department of Chemistry,College of Chemistry and Chemical Engineering,Xiamen University,Xiamen 361005,China |
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| Abstract: | Starting from the oxygenated piperidine building block 20,two synthetic approaches to new building blocks(8R,8aS) -and(8R,8aR) -8-hydroxy-5-indolizidinones 19a/19b and 15a/15b have been developed,respectively. The first one is based on the trans-diastereoselective reductive alkylation(dr=93:7) ,followed by a four-step procedure;and the second one called for the RCM reaction on the N,O-acetal derived from a vinylation,which was followed by a pyrrole formation,and a stereocontrolled cis-selective(dr=91:9) cat... |
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| Keywords: | indolizidines building blocks enantioselective synthesis RCM reaction catalytic hydrogenation |
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