通过不对称羟醛缩合反应合成生物活性天然产物
Synthesis of Bioactive Natural Products by Asymmetric - and -Aldol Reactions.
作者信息
Ghosh Arun K, Dawson Zachary L
机构信息
Departments of Chemistry and Medicinal Chemistry, Purdue University, West Lafayette, IN 47907, USA Fax +1(765)4961612;
出版信息
Synthesis (Stuttg). 2009 Sep;2009(17):2992-3002. doi: 10.1055/s-0029-1216941.
Abstract
The use of several variants of the asymmetric aldol reaction as key steps in the syntheses of bioactive target molecules is described.
摘要
本文描述了几种不对称羟醛缩合反应变体在生物活性目标分子合成中作为关键步骤的应用。
相似文献
1
Synthesis of Bioactive Natural Products by Asymmetric - and -Aldol Reactions.通过不对称羟醛缩合反应合成生物活性天然产物
Synthesis (Stuttg). 2009 Sep;2009(17):2992-3002. doi: 10.1055/s-0029-1216941.
2
Transition state models for probing stereoinduction in Evans chiral auxiliary-based asymmetric aldol reactions.用于探测 Evans 手性辅助剂不对称醛醇反应中立体诱导的过渡态模型。
J Am Chem Soc. 2010 Sep 8;132(35):12319-30. doi: 10.1021/ja101913k.
3
Boron-mediated aldol reaction of carboxylic esters: complementary anti- and syn-selective asymmetric aldol reactions.硼介导的羧酸酯的羟醛反应：互补的反式和顺式选择性不对称羟醛反应
J Org Chem. 2002 Jul 26;67(15):5250-6. doi: 10.1021/jo0257896.
4
A temporary stereocentre approach for the asymmetric synthesis of chiral cyclopropane-carboxaldehydes.一种用于手性环丙烷 - 甲醛不对称合成的临时立体中心方法。
Org Biomol Chem. 2009 Sep 7;7(17):3537-48. doi: 10.1039/b908600e. Epub 2009 Jul 8.
5
Remote Asymmetric Induction Reactions using a E, E-Vinylketene Silyl N, O-Acetal and the Wide Range Stereocontrol Strategy for the Synthesis of Polypropionates.使用E，E-乙烯基酮硅基N，O-缩醛的远程不对称诱导反应以及用于合成聚丙酸酯的广泛立体控制策略。
Acc Chem Res. 2018 May 15;51(5):1301-1314. doi: 10.1021/acs.accounts.8b00125. Epub 2018 May 4.
6
Solid-phase asymmetric synthesis using a polymer-supported chiral Evans'-type oxazolidin-2-one.采用聚合物支载的手性 Evans 型恶唑烷-2-酮的固相不对称合成。
Nat Protoc. 2013 Oct;8(10):1890-906. doi: 10.1038/nprot.2013.025. Epub 2013 Sep 12.
7
Stereoregulations of pyrimidinone based chiral auxiliary in aldol and alkylation reactions: a convenient route to oxyneolignans.基于嘧啶酮手性辅基的立体调控在Aldol 和烷基化反应中的应用：一种构建氧新木脂素的便捷途径。
Org Lett. 2012 Nov 16;14(22):5672-5. doi: 10.1021/ol302653g. Epub 2012 Oct 30.
8
A designer axially chiral amino sulfonamide as an efficient organocatalyst for direct asymmetric anti-selective Mannich reactions and syn-selective cross-aldol reactions.一种设计的轴向手性氨基磺酰胺，作为用于直接不对称反选择性曼尼希反应和顺式选择性交叉羟醛缩合反应的高效有机催化剂。
Chemistry. 2009 Jul 6;15(27):6678-87. doi: 10.1002/chem.200900267.
9
Synthesis of sialic acid derivatives based on chiral substrate-controlled stereoselective aldol reactions using pyruvic acid oxabicyclo[2.2.2]octyl orthoester.基于使用丙酮酸氧杂双环[2.2.2]辛酯的手性底物控制的立体选择性羟醛反应合成唾液酸衍生物。
Org Biomol Chem. 2017 Jan 18;15(3):640-648. doi: 10.1039/c6ob02412b.
10
Two-Pot Synthesis of Chiral 1,3-syn-Diols through Asymmetric Organocatalytic Aldol and Wittig Reactions Followed by Domino Hemiacetal/Oxy-Michael Reactions.通过不对称有机催化羟醛缩合反应和维蒂希反应，随后进行多米诺半缩醛/氧-迈克尔反应实现手性1,3-顺式二醇的双釜合成。
Chemistry. 2018 Apr 3;24(19):4909-4915. doi: 10.1002/chem.201705930. Epub 2018 Mar 2.
引用本文的文献
1
Simple Preparation of Tetrazole Chitosan Derivatives Which Exhibit High Catalytic and Antibacterial Activity.具有高催化和抗菌活性的四氮唑壳聚糖衍生物的简易制备方法。
Polymers (Basel). 2025 Jun 14;17(12):1657. doi: 10.3390/polym17121657.
2
Catalytic Reductive Aldol and Mannich Reactions of Enone, Acrylate, and Vinyl Heteroaromatic Pronucleophiles.烯酮、丙烯酸盐和乙烯基杂芳烃给电子体的催化还原Aldol 和 Mannich 反应。
Chem Rev. 2020 Apr 22;120(8):3721-3748. doi: 10.1021/acs.chemrev.0c00053. Epub 2020 Mar 19.
3
Highly Stereoselective Asymmetric Aldol Routes to -Butyl-2-(3,5-difluorophenyl)-1-oxiran-2-yl)ethyl)carbamates: Building Blocks for Novel Protease Inhibitors.用于合成新型蛋白酶抑制剂的结构单元——制备叔丁基-2-(3,5-二氟苯基)-1-(环氧乙烷-2-基)乙基氨基甲酸酯的高立体选择性不对称羟醛缩合路线
Tetrahedron Lett. 2017 Oct 25;58(43):4062-4065. doi: 10.1016/j.tetlet.2017.09.025. Epub 2017 Sep 14.
4
Capturing the essence of organic synthesis: from bioactive natural products to designed molecules in today's medicine.捕捉有机合成的精髓：从生物活性天然产物到当今药物设计的分子。
J Org Chem. 2010 Dec 3;75(23):7967-89. doi: 10.1021/jo101606g. Epub 2010 Oct 11.
本文引用的文献
1
Synthetic studies of microtubule stabilizing agent peloruside A: an asymmetric synthesis of C-C segment.微管稳定剂peloruside A的合成研究：C-C片段的不对称合成
Tetrahedron Lett. 2003 Oct 6;44(41):7659-7661. doi: 10.1016/j.tetlet.2003.08.023. Epub 2003 Sep 13.
2
A Stereoselective Anti-Aldol Route to (3,3a,6a)-Hexahydrofuro[2,3-] furan-3-ol: A Key Ligand for a New Generation of HIV Protease Inhibitors.一条通往(3,3a,6a)-六氢呋喃并[2,3-]呋喃-3-醇的立体选择性反羟醛缩合路线：新一代HIV蛋白酶抑制剂的关键配体
Synthesis (Stuttg). 2006 Sep;2006(18):3015-3018. doi: 10.1055/s-2006-942547.
3
An enantioselective synthesis of the C-C segment of antitumor macrolide peloruside A.抗肿瘤大环内酯类化合物peloruside A碳-碳片段的对映选择性合成。
Tetrahedron Lett. 2003 May 12;44(20):3967-3969. doi: 10.1016/S0040-4039(03)00744-5. Epub 2003 Apr 24.
4
Synthesis of Enantiomerically Pure Anti-Aldols: A Highly Stereoselective Ester-Derived Titanium Enolate Aldol Reaction.对映体纯的反式醛醇缩合物的合成：一种高度立体选择性的酯衍生钛烯醇盐醛醇缩合反应。
J Am Chem Soc. 1996 Mar 13;118(10):2527-2528. doi: 10.1021/ja9539148.
5
Highly Enantioselective Aldol Reaction: Development of a New Chiral Auxiliary from -1-Amino-2-hydroxyindan.高度对映选择性羟醛反应：基于-1-氨基-2-羟基茚开发新型手性助剂
J Chem Soc Chem Commun. 1992;1992(22):1673-1674. doi: 10.1039/C39920001673.
6
A Convergent, Enantioselective Total Synthesis of Hapalosin: A Drug with Multidrug-Resistance Reversing Activity.哈帕洛辛的汇聚式对映选择性全合成：一种具有多药耐药逆转活性的药物。
Angew Chem Int Ed Engl. 1996 Jan 19;35(1):74-76. doi: 10.1002/anie.199600741.
7
SYNTHESIS AND OPTICAL RESOLUTION OF HIGH AFFINITY P-LIGANDS FOR HIV-1 PROTEASE INHIBITORS.HIV-1蛋白酶抑制剂高亲和力P-配体的合成与光学拆分
Tetrahedron Lett. 1995 Jan 23;36(4):505-508. doi: 10.1016/0040-4039(94)02296-N. Epub 2000 Jun 14.
8
A convergent synthesis of the proposed structure of antitumor depsipeptide stereocalpin A.抗肿瘤缩肽立体钙平A提出结构的汇聚合成。
Org Lett. 2009 May 7;11(9):1963-6. doi: 10.1021/ol900412u.
9
L-selectride-mediated highly diastereoselective asymmetric reductive aldol reaction: access to an important subunit for bioactive molecules.L-选择氢化物介导的高度非对映选择性不对称还原羟醛反应：获得生物活性分子的一个重要亚基。
Org Lett. 2008 Nov 6;10(21):4811-4. doi: 10.1021/ol801971t. Epub 2008 Oct 3.
10
Enantioselective total synthesis of peloruside A: a potent microtubule stabilizer.海葵毒素A的对映选择性全合成：一种有效的微管稳定剂。
Org Lett. 2008 Mar 6;10(5):1001-4. doi: 10.1021/ol703091b. Epub 2008 Feb 5.
Zotero 插件