简明对映选择性合成氯磺脂酸马尔哈门脂磷 A。
A concise enantioselective synthesis of the chlorosulfolipid malhamensilipin A.
机构信息
Department of Chemistry, University of California, Irvine, California 92697, USA.
出版信息
J Am Chem Soc. 2010 Mar 3;132(8):2542-3. doi: 10.1021/ja910809c.
Abstract
The first enantioselective synthesis of a member of the chlorosulfolipid family of natural products is reported. All of the polar substituents of malhamensilipin A are introduced with high stereoselectivity, and the unique (E)-chlorovinyl sulfate is created by a chemo-, regio-, and stereoselective E2 elimination of HCl in a reaction that likely has a counterpart in the biosynthesis of this fascinating natural product.
摘要
首次报道了一种氯磺酸脂类天然产物的对映选择性合成。马拉门斯林 A 的所有极性取代基均具有高立体选择性地引入，独特的（E）-氯代乙烯基硫酸盐是通过反应中 HCl 的化学选择性、区域选择性和立体选择性 E2 消除形成的，该反应可能在这种迷人的天然产物的生物合成中具有对应物。
相似文献
1
A concise enantioselective synthesis of the chlorosulfolipid malhamensilipin A.简明对映选择性合成氯磺脂酸马尔哈门脂磷 A。
J Am Chem Soc. 2010 Mar 3;132(8):2542-3. doi: 10.1021/ja910809c.
2
Structure of malhamensilipin A, an inhibitor of protein tyrosine kinase, from the cultured chrysophyte Poterioochromonas malhamensis.
J Nat Prod. 1994 Apr;57(4):524-7. doi: 10.1021/np50106a015.
3
Structure revision and absolute configuration of malhamensilipin A from the freshwater chrysophyte Poterioochromonas malhamensis.淡水甲藻 Poterioochromonas malhamensis 中马哈姆烯素 A 的结构修饰和绝对构型。
J Nat Prod. 2010 Feb 26;73(2):279-83. doi: 10.1021/np900672h.
4
Catalytic Enantioselective Dihalogenation and the Selective Synthesis of (-)-Deschloromytilipin A and (-)-Danicalipin A.催化对映选择性二卤化反应及（-）-去氯米蒂利平A和（-）-达尼卡利平A的选择性合成
J Am Chem Soc. 2016 Apr 20;138(15):5150-8. doi: 10.1021/jacs.6b01643. Epub 2016 Apr 8.
5
A synthesis of the chlorosulfolipid mytilipin A via a longest linear sequence of seven steps.经最长线性序列的七步反应合成氯化磺脂 mytilipin A。
Angew Chem Int Ed Engl. 2013 Sep 16;52(38):10052-5. doi: 10.1002/anie.201304565. Epub 2013 Aug 8.
6
Natural product biosynthesis inspired concise and stereoselective synthesis of benzopyrones and related scaffolds.天然产物生物合成启发的苯并吡喃类化合物及相关骨架的简洁和立体选择性合成。
Org Lett. 2011 Apr 15;13(8):1988-91. doi: 10.1021/ol200389p. Epub 2011 Mar 18.
7
Enantioselective total synthesis of plectosphaeroic acid B.对映选择性全合成聚球藻酸 B。
J Am Chem Soc. 2013 Mar 20;135(11):4231-4. doi: 10.1021/ja401423j. Epub 2013 Mar 6.
8
Enantioselective formation of quaternary carbon stereocenters in natural product synthesis: a recent update.手性中心的对映选择性形成在天然产物合成中的应用：最新进展。
Nat Prod Rep. 2020 Feb 26;37(2):276-292. doi: 10.1039/c9np00039a.
9
Enantioselective synthesis of all stereoisomers of geosmin and of biosynthetically related natural products.对土腥素及其生物合成相关天然产物的所有立体异构体进行对映选择性合成。
Org Biomol Chem. 2024 Jul 17;22(28):5748-5758. doi: 10.1039/d4ob00934g.
10
Synthesis of 9-Dechlorochrysophaentin A Enables Studies Revealing Bacterial Cell Wall Biosynthesis Inhibition Phenotype in .9-去氯金钗石斛甲素的合成使研究能够揭示其在. 中的细菌细胞壁生物合成抑制表型。
J Am Chem Soc. 2020 Sep 23;142(38):16161-16166. doi: 10.1021/jacs.0c04917. Epub 2020 Sep 8.
引用本文的文献
1
Stereospecific syn-dihalogenations and regiodivergent syn-interhalogenation of alkenes via vicinal double electrophilic activation strategy.通过邻位双亲电活化策略实现烯烃的立体选择性顺式二卤代反应和区域发散性顺式卤间代反应。
Nat Commun. 2024 May 2;15(1):3710. doi: 10.1038/s41467-024-47942-w.
2
The Recurring Roles of Chlorine in Synthetic and Biological Studies of the Lissoclimides.氯在 Lissoclimides 的合成和生物研究中的反复作用。
Acc Chem Res. 2021 Mar 2;54(5):1131-1142. doi: 10.1021/acs.accounts.0c00866. Epub 2021 Feb 5.
3
Organoselenium-catalyzed enantioselective -dichlorination of unbiased alkenes.有机硒催化的未活化烯烃的对映选择性α,α-二氯化反应。
Tetrahedron. 2019 Jul 2;75(31):4086-4098. doi: 10.1016/j.tet.2019.05.054. Epub 2019 Jun 1.
4
Synthesis of malhamensilipin A exploiting iterative epoxidation/chlorination: experimental and computational analysis of epoxide-derived chloronium ions.利用迭代环氧化/氯化反应合成马尔哈门西利平A：环氧化物衍生的氯鎓离子的实验与计算分析
Chem Sci. 2016 Dec 11;7(12):7040-7049. doi: 10.1039/c6sc03012b. Epub 2016 Aug 2.
5
Catalytic Enantioselective Dihalogenation and the Selective Synthesis of (-)-Deschloromytilipin A and (-)-Danicalipin A.催化对映选择性二卤化反应及（-）-去氯米蒂利平A和（-）-达尼卡利平A的选择性合成
J Am Chem Soc. 2016 Apr 20;138(15):5150-8. doi: 10.1021/jacs.6b01643. Epub 2016 Apr 8.
6
Stereoselective Halogenation in Natural Product Synthesis.天然产物合成中的立体选择性卤化反应
Angew Chem Int Ed Engl. 2016 Mar 24;55(14):4396-434. doi: 10.1002/anie.201506388. Epub 2016 Feb 2.
7
Triphosgene-pyridine mediated stereoselective chlorination of acyclic aliphatic 1,3-diols.三光气-吡啶介导的无环脂肪族1,3-二醇的立体选择性氯化反应
Chem Commun (Camb). 2015 Oct 18;51(81):15075-8. doi: 10.1039/c5cc06365e.
8
Enantioselective divergent syntheses of several polyhalogenated Plocamium monoterpenes and evaluation of their selectivity for solid tumors.几种多卤代蕨藻单萜的对映选择性发散合成及其对实体瘤的选择性评估。
Angew Chem Int Ed Engl. 2014 Nov 3;53(45):12205-9. doi: 10.1002/anie.201407726. Epub 2014 Sep 12.
9
General approach to the synthesis of the chlorosulfolipids danicalipin A, mytilipin A, and malhamensilipin A in enantioenriched form.以对映体富集形式合成氯代硫脂类化合物达尼卡利平A、贻贝脂素A和马尔哈门脂素A的通用方法。
J Org Chem. 2014 Mar 7;79(5):2226-41. doi: 10.1021/jo5000829. Epub 2014 Feb 13.
10
Approaches to the chemical synthesis of the chlorosulfolipids.氯磺酸酯的化学合成方法。
Acc Chem Res. 2014 Feb 18;47(2):718-28. doi: 10.1021/ar400246w. Epub 2014 Jan 8.
本文引用的文献
1
Structure revision and absolute configuration of malhamensilipin A from the freshwater chrysophyte Poterioochromonas malhamensis.淡水甲藻 Poterioochromonas malhamensis 中马哈姆烯素 A 的结构修饰和绝对构型。
J Nat Prod. 2010 Feb 26;73(2):279-83. doi: 10.1021/np900672h.
2
Conformational and configurational analysis in the study and synthesis of chlorinated natural products.在氯化天然产物的研究和合成中进行构象和构型分析。
J Am Chem Soc. 2009 Nov 4;131(43):15866-76. doi: 10.1021/ja906461h.
3
Relative stereochemistry determination and synthesis of the major chlorosulfolipid from Ochromonas danica.嗜铬绿藻中主要氯代硫脂的相对立体化学测定与合成
J Am Chem Soc. 2009 Jun 10;131(22):7570-2. doi: 10.1021/ja902138w.
4
Total synthesis of a chlorosulpholipid cytotoxin associated with seafood poisoning.一种与海鲜中毒相关的氯代硫脂细胞毒素的全合成。
Nature. 2009 Jan 29;457(7229):573-6. doi: 10.1038/nature07734.
5
Synthesis and characterization of all four diastereomers of 3,4-dichloro-2-pentanol, motifs relevant to the chlorosulfolipids.合成并表征 3,4-二氯-2-戊醇的全部四个非对映异构体，这些异构体与氯磺酸脂有关。
J Org Chem. 2009 Mar 6;74(5):2175-8. doi: 10.1021/jo802390e.
6
Enantiocontrolled synthesis of polychlorinated hydrocarbon motifs: a nucleophilic multiple chlorination process revisited.
J Org Chem. 2009 Jan 16;74(2):696-702. doi: 10.1021/jo802093d.
7
Stereoselective dichlorination of allylic alcohol derivatives to access key stereochemical arrays of the chlorosulfolipids.烯丙醇衍生物的立体选择性二氯化反应以获取氯代硫脂的关键立体化学阵列。
J Am Chem Soc. 2008 Sep 17;130(37):12514-8. doi: 10.1021/ja804167v. Epub 2008 Aug 22.
8
Structure and stereochemistry of a new cytotoxic polychlorinated sulfolipid from Adriatic shellfish.一种来自亚得里亚海贝类的新型细胞毒性多氯代硫脂的结构与立体化学
J Am Chem Soc. 2002 Nov 6;124(44):13114-20. doi: 10.1021/ja0207347.
9
Structural elucidation of a new cytotoxin isolated from mussels of the Adriatic sea.从亚得里亚海贻贝中分离出的一种新细胞毒素的结构解析。
J Org Chem. 2001 Jan 26;66(2):578-82. doi: 10.1021/jo001437s.
10
Stereoselective preparation of ceramide and its skeleton backbone modified analogues via cyclic thionocarbonate intermediates derived by catalytic asymmetric dihydroxylation of alpha,beta-unsaturated ester precursors.
J Org Chem. 2000 Nov 3;65(22):7627-33. doi: 10.1021/jo001226n.
Zotero 插件