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Towards Stereochemical Control＂ Two Approaches for the Highly *** Construction of the Spirolactone Moieties of Some Stemona Alkaloids

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Chinese Journal of Chemistry 2013年第1期31卷 55-62页

作者： Shichuan Tuo Xuekui Liu peiqiang huang Department of Chemistry and Fujian Provincial Key Laboratory for Chemical Biology College of Chemistry and Chemical Engineering Xiamen University Xiamen Fujian 361005 China

Some Stemona alkaloids belonging to the tuberostemospironine group possess a spirolactone moiety with anti-configuration （C-9/C-9a）. In this paper, we describe two approaches to this structural unity. By using bromine atom as a traceless directing group, the SmI2-mediated reductive coupling of ketone 6 and fl-bromomethacrylate proceeded with complete anti-diastereoselectivity. In the absence of an a-directing （chelation） group, the one-pot reaction of the ketone derived from alcohol 15 with the organozinc reagent generated from bromomethacrylate af- forded spiro-a-methylene-y-lactone derivative 16 as a single diastereomer. These two highly diastereoselective methods would find application in the synthesis of stemona alkaloids containing anti-configured spiro-lactone/pyr- rolidine moieties. In addition, on the basis of our previous work, the total synthesis of （-）-9-epi-11-demethyl- sessilifoliamide J （11）, and an improved synthesis of （-）-9,11-di-epi-sessilifoliamide J （9） were accomplished.

关键词： Stemona alkaloids spirolactone SmI2 organozinc reagent sessilifoliamide J

Generation and α-hydroxyalkylation of a novel 3-piperidinol N-α-carbanion intermediate

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Science China Chemistry 2009年第10期52卷 1631-1638页

作者： ZHENG Xiao CHEN Guo RUAN YuanPing huang peiqiang Department of Chemistry and Key Laboratory for Chemical Biology of Fujian Province College of Chemistry and Chemical EngineeringXiamen UniversityXiamen 361005China

The (S)-sulfide 6 has been synthesized as a synthetic equivalent of novel 3-piperidinol N-α-carbanion B via deprotonation and lithium naphthanelide (LN)-mediated reductive lithiation. The reaction of the 3-piperidinol N-α-carbanion intermediate B with carbonyl compounds gave, besides some reduced product 2a, the desired α-hydroxyalkylation products 12-17 with excellent 2,3-diastereoselectivity. The reductive α-hydroxyalkylation with unsymmetric carbonyl compounds led to only 50:50 to 77:23 diastereoselectivities at the C-1' carbinol center.

关键词： sulfide N-α-carbanion lithium-naphthanelide reductive lithiation carbonyl compounds α-hydroxyalkylation diastereoselectivity

Progress on the total synthesis of natural products in China:From 2006 to 2010

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Science China Chemistry 2012年第7期55卷 1175-1212页

作者： CHEN Jie WANG AiE HUO HaoHua huang peiqiang Department of Chemistry and Fujian Provincial Key Laboratory of Chemical Biology College of Chemistry and Chemical EngineeringXiamen UniversityXiamen 361005China

This paper summarizes the progress on the total syntheses riod from 2006 to 2010. The overview focuses on the first of natural products accomplished in rnainland China during the petotal synthesis of natural products of contemporary interest includ- ing alkaloids, cyclopeptides and cyclic depsipeptides, macrolides, terpenoids and steroids, saponins and glycosides. The development of novel synthetic strategies and methodologies, and application of new selective synthetic methods in the total syntheses of natural products are included as well.

关键词： natural products total synthesis review China's Mainland

Asymmetric syntheses of (8R,8aS)- and (8R,8aR)-8-hydroxy-5-indolizidinones:Two promising oxygenated indolizidine building blocks

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Science China Chemistry 2011年第4期54卷 737-744页

作者： ZHANG HongKui LI Xin huang huang huang peiqiang Department of Chemistry and Key Laboratory for Chemical Biology of Fujian Province College of Chemistry and Chemical EngineeringXiamen UniversityXiamen. China

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) catalytic hydrogenation. Reduction of the diastereomer 15a produced (8R,8aR)-8-indolizidinol (18).

关键词： indolizidines building blocks diastereoselective synthesis RCM reaction catalytic hydrogenation

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基于苹果酰亚胺的不对称合成方法学研究进展

有机化学 2001年第11期21卷 1065-1073页

作者：黄培强厦门大学化学系，厦门361005

综述了以苹果酰亚胺为手性吡咯烷(酮)合成子等效体的合成方法学研究进展.通过新建立的高度区域和立体选择性的灵活多用的不对称还原烷基化方法,可方便地合成反式-5-烷基-4-羟基-2-吡咯烷酮,进而转化为反式-2-烷基-3-羟基(胺基)吡咯烷和... 详细信息

综述了以苹果酰亚胺为手性吡咯烷(酮)合成子等效体的合成方法学研究进展.通过新建立的高度区域和立体选择性的灵活多用的不对称还原烷基化方法,可方便地合成反式-5-烷基-4-羟基-2-吡咯烷酮,进而转化为反式-2-烷基-3-羟基(胺基)吡咯烷和反侧-γ-烷基-γ-氨基-β-羟基酸.由此打开了通向依莫必利,茴香霉素,pyrrolam A,hapalosin的γ-氨基酸片断和statine类似物(3S,4R)-ACHPA活化形式的多用途合成路线.

关键词：还原烷基化 2-吡咯烷酮不对称合成苹果酰亚胺药物中间体依莫必利茴香霉素

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D-奎尼酸:一个多用途的手性合成子

有机化学 1999年第4期19卷 364-373页

作者：黄培强厦门大学化学系厦门361005

综述了D-奎尼酸在各种环状和链状生物活性化合物合成中的应用。奎尼酸分子中特有的顺式γ-羟基羧酸的结构单元提供了区别分子中各种羟基,以及进行其它区域选择性和立体选择性控制的方便途经。奎尼酸的结构特征以及其价廉、易得的优点,... 详细信息

综述了D-奎尼酸在各种环状和链状生物活性化合物合成中的应用。奎尼酸分子中特有的顺式γ-羟基羧酸的结构单元提供了区别分子中各种羟基,以及进行其它区域选择性和立体选择性控制的方便途经。奎尼酸的结构特征以及其价廉、易得的优点,使之成为一个有用的而且重要的手性合成子。

关键词： D-奎尼酸对映纯 EPC 奎尼酸合成手性合成子

Radical Chemistry: An Indispensable Tool for the Synthesis of Alkaloids and N-Containing Bioactive Compounds

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Radical Chemistry: An Indispensable Tool for the Synthesis o...

中国化学会第二届全国有机自由基化学会议

作者： peiqiang huang Department of Chemistry College of Chemistry and Chemical Engineering Xiamen University

＜正＞α-Aminoalkyl radicals are a class of valuable and some times indispensible reactive intermediates for C-C bond formation reactions. In this talk, four α-aminoalkyl radical-based C-C bond forming methods（eq. 1-4 in Scheme） and the synthesis of alkaloids, analogs and intermediates employing radical chemistry as an indispensable tool will be presented.1

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仲酰胺经酰胺活化直接合成酮的普适性方法

化学学报 2012年第18期70卷 1917-1922页

作者：肖开炯黄应红黄培强化学生物学福建省重点实验室厦门大学化学化工学院化学系厦门361005

本文报道仲酰胺经去胺基烷基化反应直接合成酮的通用性方法.这一新的C—C键形成方法是基于Tf2O对仲酰胺的活化及有机铈试剂对活化所形成活性中间体的加成而实现的.该方法可用于各种酮的合成,包括烷基-烷基酮、烷基-芳基酮、芳基-芳基酮... 详细信息

本文报道仲酰胺经去胺基烷基化反应直接合成酮的通用性方法.这一新的C—C键形成方法是基于Tf2O对仲酰胺的活化及有机铈试剂对活化所形成活性中间体的加成而实现的.该方法可用于各种酮的合成,包括烷基-烷基酮、烷基-芳基酮、芳基-芳基酮、α,β-不饱和酮以及β-氯-α,β-不饱和酮等,收率65%～90%.研究表明,除了有机铈试剂外,碱性较弱的炔基硼试剂、温和亲核性的烯丙基三甲基硅烷以及低亲核性的苯乙烯均可与仲酰胺的活化中间体进行加成反应,水解后生成相应的酮.因此,该方法具有较好的普适性和重要的合成应用价值.基于实验结果和验证实验,提出经由腈鎓中间体的可能反应机理.本法使仲酰胺成为形式上的酰化试剂,不但可与有机金属试剂反应,还可与烯丙基三甲基硅烷和苯乙烯进行还原酰化反应.

关键词：仲酰胺酮有机铈试剂分子活化 C—C键形成还原酰化

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天然产物的仿生全合成:回顾与展望