Diastereoselective Total Synthesis of the Vancomycin Aglycon with Ordered Atropisomer Equilibrations
- Dale L. Boger ,
- Susumu Miyazaki ,
- Seong Heon Kim ,
- Jason H. Wu ,
- Olivier Loiseleur , and
- Steven L. Castle
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- Sabine Boisnard,, Luc Neuville,, Michèle Bois-Choussy, and, Jieping Zhu. Asymmetric Synthesis of Actinoidic Acid Derivatives. Organic Letters 2000, 2 (16) , 2459-2462. https://doi.org/10.1021/ol006110s
- Dale L. Boger,, Susumu Miyazaki,, Seong Heon Kim,, Jason H. Wu,, Steven L. Castle,, Olivier Loiseleur, and, Qing Jin. Total Synthesis of the Vancomycin Aglycon. Journal of the American Chemical Society 1999, 121 (43) , 10004-10011. https://doi.org/10.1021/ja992577q
- Pedro N. Batalha, Luana S.M. Forezi, Carolina G.S. Lima, Fernanda P. Pauli, Fernanda C.S. Boechat, Maria Cecília B.V. de Souza, Anna C. Cunha, Vitor F. Ferreira, Fernando de C. da Silva. Drug repurposing for the treatment of COVID-19: Pharmacological aspects and synthetic approaches. Bioorganic Chemistry 2021, 106 , 104488. https://doi.org/10.1016/j.bioorg.2020.104488
- A. R. Gataullina, R. R. Gataullin. Axial Chiral Metal Complexes, Carbo- and Heterocycles: Modern Synthesis Strategies and Examples of the Effect of Atropoisomerism on the Structure of Reaction Products. Russian Journal of General Chemistry 2020, 90 (7) , 1255-1284. https://doi.org/10.1134/S1070363220070130
- F. Wieland Goetzke, Lucy Dijk, Stephen P. Fletcher. Catalytic Asymmetric S uzuki– M iyaura Couplings. 2019,,, 1-54. https://doi.org/10.1002/9780470682531.pat0962
- Zhi-Chen Wu, Dale L. Boger. Exploration of the site-specific nature and generalizability of a trimethylammonium salt modification on vancomycin: A-ring derivatives. Tetrahedron 2019, 75 (24) , 3160-3165. https://doi.org/10.1016/j.tet.2019.02.008
- Fuzhuo Li, Xiao Zhang, Hans Renata. Enzymatic C H functionalizations for natural product synthesis. Current Opinion in Chemical Biology 2019, 49 , 25-32. https://doi.org/10.1016/j.cbpa.2018.09.004
- Robert M. Williams, Yusuke Amino. Synthesis of Orthogonally Protected Actinoidic Acid Trimethyl Ether. HETEROCYCLES 2019, 99 (1) , 83. https://doi.org/10.3987/COM-18-S(F)2
- Pei-Qiang Huang. Principles for Synthetic Efficiency and Expansion of the Field. 2018,,, 27-65. https://doi.org/10.1002/9781118940228.ch1
- Andrew Giltrap. Introduction. 2018,,, 1-31. https://doi.org/10.1007/978-981-10-8806-3_1
- Yuanjun Sun, Yahui Ding, Dongmei Li, Ruifei Zhou, Xiuwen Su, Juan Yang, Xiaoqian Guo, Chuanke Chong, Jinghan Wang, Weicheng Zhang, Cuigai Bai, Liang Wang, Yue Chen. Cyclic Depsipeptide BE-43547A 2 : Synthesis and Activity against Pancreatic Cancer Stem Cells. Angewandte Chemie 2017, 129 (46) , 14819-14823. https://doi.org/10.1002/ange.201709744
- Yuanjun Sun, Yahui Ding, Dongmei Li, Ruifei Zhou, Xiuwen Su, Juan Yang, Xiaoqian Guo, Chuanke Chong, Jinghan Wang, Weicheng Zhang, Cuigai Bai, Liang Wang, Yue Chen. Cyclic Depsipeptide BE-43547A 2 : Synthesis and Activity against Pancreatic Cancer Stem Cells. Angewandte Chemie International Edition 2017, 56 (46) , 14627-14631. https://doi.org/10.1002/anie.201709744
- Oleg M. Demchuk, Katarzyna Kapłon, Agnieszka Kącka, K. Michał Pietrusiewicz. The utilization of chiral phosphorus ligands in atroposelective cross-coupling reactions. Phosphorus, Sulfur, and Silicon and the Related Elements 2016, 191 (2) , 180-200. https://doi.org/10.1080/10426507.2015.1079197
- A.L. Brown, N.L. Fifer, L. Hunter, Q.I. Churches, P.W.H. Chan, S.B. Cohen, C.A. Hutton. Total Synthesis of Ustiloxin D. 2016,,, 169-191. https://doi.org/10.1016/B978-0-08-100756-3.00006-6
- Anny Jutand, Guillaume Lefèvre. Transition Metal-Catalyzed Carbon-Carbon Cross-Coupling. 2015,,, 511-545. https://doi.org/10.1002/9781118754887.ch19
- Kiyoun Lee, Yam B. Poudel, Christopher M. Glinkerman, Dale L. Boger. Total synthesis of dihydrolysergic acid and dihydrolysergol: development of a divergent synthetic strategy applicable to rapid assembly of D-ring analogs. Tetrahedron 2015, 71 (35) , 5897-5905. https://doi.org/10.1016/j.tet.2015.05.093
- Mark S Butler, Karl A Hansford, Mark A T Blaskovich, Reena Halai, Matthew A Cooper. Glycopeptide antibiotics: Back to the future. The Journal of Antibiotics 2014, 67 (9) , 631-644. https://doi.org/10.1038/ja.2014.111
- Jiyong Hong. Natural Product Synthesis at the Interface of Chemistry and Biology. Chemistry - A European Journal 2014, 20 (33) , 10204-10212. https://doi.org/10.1002/chem.201402804
- K. C. Nicolaou, Christopher R. H. Hale. The endeavor of total synthesis and its impact on chemistry, biology and medicine. National Science Review 2014, 1 (2) , 233-252. https://doi.org/10.1093/nsr/nwu001
- Armin Bauer, Mark Brönstrup. Industrial natural product chemistry for drug discovery and development. Nat. Prod. Rep. 2014, 31 (1) , 35-60. https://doi.org/10.1039/C3NP70058E
- Eugenia N Olsufyeva, Maria N Preobrazhenskaya. Glycopeptide antibiotic analogs efficient against vancomycin-resistant bacteria: a patent evaluation (WO2013022763). Expert Opinion on Therapeutic Patents 2013, 23 (12) , 1625-1634. https://doi.org/10.1517/13543776.2013.831074
- Joseph R. Pinchman, Dale L. Boger. Investigation into the functional impact of the vancomycin C-ring aryl chloride. Bioorganic & Medicinal Chemistry Letters 2013, 23 (17) , 4817-4819. https://doi.org/10.1016/j.bmcl.2013.06.080
- Steven L. Castle, Bing Ma. Total Synthesis of the Unusual Peptide Celogentin C. 2013,,, 45-77. https://doi.org/10.1016/B978-0-08-099362-1.00002-3
- B.E. Maryanoff, M.N. Greco. 1.7 Stereochemical Lability in Drug Molecules: Cases Where Chirality May Not Be Critical for Drug Development. 2012,,, 105-119. https://doi.org/10.1016/B978-0-08-095167-6.00105-1
- K. C. Nicolaou, Christopher R. H. Hale, Christian Nilewski, Heraklidia A. Ioannidou. Constructing molecular complexity and diversity: total synthesis of natural products of biological and medicinal importance. Chemical Society Reviews 2012, 41 (15) , 5185. https://doi.org/10.1039/c2cs35116a
- Yun Xuan Tan, Floyd E. Romesberg. Latent antibiotics and the potential of the arylomycins for broad-spectrum antibacterial activity. MedChemComm 2012, 3 (8) , 916. https://doi.org/10.1039/c2md20043k
- Tanja Gulder, Phil S. Baran. Strained cyclophane natural products: Macrocyclization at its limits. Natural Product Reports 2012, 29 (8) , 899. https://doi.org/10.1039/c2np20034a
- Timo Leermann, Pierre-Emmanuel Broutin, Frédéric R. Leroux, Françoise Colobert. Construction of the biaryl-part of vancomycin aglycon via atropo-diastereoselective Suzuki–Miyaura coupling. Organic & Biomolecular Chemistry 2012, 10 (20) , 4095. https://doi.org/10.1039/c2ob25373a
- Hans-Dieter Arndt, Roman Lichtenecker, Patrick Loos, Lech-Gustav Milroy. Biomimetic Synthesis of Azole- and Aryl-Peptide Alkaloids. 2011,,, 317-355. https://doi.org/10.1002/9783527634606.ch9
- Stephen A. Habay, Steve S. Park, Steven M. Kennedy, A. Richard Chamberlin. Methods for the Chemical Synthesis of Noncoded α-Amino Acids found in Natural Product Peptides. 2010,,, 163-243. https://doi.org/10.1002/9783527631766.ch5
- Alex M. Szpilman, Erick M. Carreira. Untersuchung der Biologie von Naturstoffen: systematische Strukturvariation durch umgelenkte Totalsynthese. Angewandte Chemie 2010, 122 (50) , 9786-9823. https://doi.org/10.1002/ange.200904761
- Alex M. Szpilman, Erick M. Carreira. Probing the Biology of Natural Products: Molecular Editing by Diverted Total Synthesis. Angewandte Chemie International Edition 2010, 49 (50) , 9592-9628. https://doi.org/10.1002/anie.200904761
- Elena Sperotto, Gerard P.M. van Klink, Johannes G. de Vries, Gerard van Koten. Aminoarenethiolato-copper(I) as (pre-)catalyst for the synthesis of diaryl ethers from aryl bromides and sequential C–O/C–S and C–N/C–S cross coupling reactions. Tetrahedron 2010, 66 (46) , 9009-9020. https://doi.org/10.1016/j.tet.2010.09.019
- Jonathan Clayden, Wesley J. Moran, Paul J. Edwards, Steven R. LaPlante. Atropisomerie als Herausforderung in der Medikamentenentwicklung. Angewandte Chemie 2009, 121 (35) , 6516-6520. https://doi.org/10.1002/ange.200901719
- Jonathan Clayden, Wesley J. Moran, Paul J. Edwards, Steven R. LaPlante. The Challenge of Atropisomerism in Drug Discovery. Angewandte Chemie International Edition 2009, 48 (35) , 6398-6401. https://doi.org/10.1002/anie.200901719
- K.C. Nicolaou, Jason S. Chen, Stephen M. Dalby. From nature to the laboratory and into the clinic. Bioorganic & Medicinal Chemistry 2009, 17 (6) , 2290-2303. https://doi.org/10.1016/j.bmc.2008.10.089
- K. C. Nicolaou, Jason S. Chen, David J. Edmonds, Anthony A. Estrada. Fortschritte in der Chemie und Biologie natürlicher Antibiotika. Angewandte Chemie 2009, 121 (4) , 670-732. https://doi.org/10.1002/ange.200801695
- K. C. Nicolaou, Jason S. Chen, David J. Edmonds, Anthony A. Estrada. Recent Advances in the Chemistry and Biology of Naturally Occurring Antibiotics. Angewandte Chemie International Edition 2009, 48 (4) , 660-719. https://doi.org/10.1002/anie.200801695
- Jonathan Clayden, Christopher P. Worrall, Wesley J. Moran, Madeleine Helliwell. Enantioselective Synthesis of an Atropisomeric Diaryl Ether. Angewandte Chemie 2008, 120 (17) , 3278-3281. https://doi.org/10.1002/ange.200705660
- Jonathan Clayden, Christopher P. Worrall, Wesley J. Moran, Madeleine Helliwell. Enantioselective Synthesis of an Atropisomeric Diaryl Ether. Angewandte Chemie International Edition 2008, 47 (17) , 3234-3237. https://doi.org/10.1002/anie.200705660
- Anthony J. Pearson, Diana V. Ciurea, Avdhoot Velankar. Studies toward the total synthesis of ristocetin A aglycone using arene–ruthenium complexes as SNAr substrates: construction of an advanced tricyclic intermediate. Tetrahedron Letters 2008, 49 (12) , 1922-1926. https://doi.org/10.1016/j.tetlet.2008.01.094
- Valentin Wittmann. Glycoproteins: Occurrence and Significance. 2008,,, 1735-1770. https://doi.org/10.1007/978-3-540-30429-6_43
- Clay S. Bennett, Richard J. Payne, Kathryn M. Koeller, Chi-Huey Wong. Biologically Relevant Glycopeptides: Synthesis and Applications. 2008,,, 1795-1857. https://doi.org/10.1007/978-3-540-30429-6_45
- Thisbe K. Lindhorst. Antitumor and Antimicrobial Glycoconjugates. 2008,,, 2545-2587. https://doi.org/10.1007/978-3-540-30429-6_66
- Takayuki Doi, Atsushi Kinbara, Hitoshi Inoue, Takashi Takahashi. Donor-Bound Glycosylation for Various Glycosyl Acceptors: Bidirectional Solid-Phase Semisynthesis of Vancomycin and Its Derivatives. Chemistry – An Asian Journal 2007, 2 (1) , 188-198. https://doi.org/10.1002/asia.200600301
- Peter F. Kaiser, Quentin I. Churches, Craig A. Hutton. Organoboron Reagents in the Preparation of Functionalized ?-Amino Acids. Australian Journal of Chemistry 2007, 60 (11) , 799. https://doi.org/10.1071/CH07103
- Miroslav Genov, Antonio Almorín, Pablo Espinet. Efficient Synthesis of Chiral 1,1′-Binaphthalenes by the Asymmetric Suzuki–Miyaura Reaction: Dramatic Synthetic Improvement by Simple Purification of Naphthylboronic Acids. Chemistry - A European Journal 2006, 12 (36) , 9346-9352. https://doi.org/10.1002/chem.200600616
- Franz von Nussbaum, Michael Brands, Berthold Hinzen, Stefan Weigand, Dieter Häbich. Antibakterielle Naturstoffe in der medizinischen Chemie – Exodus oder Renaissance?. Angewandte Chemie 2006, 118 (31) , 5194-5254. https://doi.org/10.1002/ange.200600350
- Franz von Nussbaum, Michael Brands, Berthold Hinzen, Stefan Weigand, Dieter Häbich. Antibacterial Natural Products in Medicinal Chemistry—Exodus or Revival?. Angewandte Chemie International Edition 2006, 45 (31) , 5072-5129. https://doi.org/10.1002/anie.200600350
- Yanxing Jia, Nianchun Ma, Zuosheng Liu, Michèle Bois-Choussy, Eduardo Gonzalez-Zamora, Adriano Malabarba, Cristina Brunati, Jieping Zhu. Design and Synthesis of Simple Macrocycles Active Against Vancomycin-ResistantEnterococci (VRE). Chemistry - A European Journal 2006, 12 (20) , 5334-5351. https://doi.org/10.1002/chem.200600137
- Qian Cai, Benli Zou, Dawei Ma. Mild Ullmann-Type Biaryl Ether Formation Reaction by Combination ofortho-Substituent and Ligand Effects. Angewandte Chemie 2006, 118 (8) , 1298-1301. https://doi.org/10.1002/ange.200503538
- Qian Cai, Benli Zou, Dawei Ma. Mild Ullmann-Type Biaryl Ether Formation Reaction by Combination ofortho-Substituent and Ligand Effects. Angewandte Chemie International Edition 2006, 45 (8) , 1276-1279. https://doi.org/10.1002/anie.200503538
- Timothy W. Wallace. Biaryl synthesis with control of axial chirality. Organic & Biomolecular Chemistry 2006, 4 (17) , 3197. https://doi.org/10.1039/b608470m
- Olivier Baudoin. The Asymmetric Suzuki Coupling Route to Axially Chiral Biaryls. European Journal of Organic Chemistry 2005, 2005 (20) , 4223-4229. https://doi.org/10.1002/ejoc.200500394
- K. C. Nicolaou, Paul G. Bulger, David Sarlah. Palladiumkatalysierte Kreuzkupplungen in der Totalsynthese. Angewandte Chemie 2005, 117 (29) , 4516-4563. https://doi.org/10.1002/ange.200500368
- K. C. Nicolaou, Paul G. Bulger, David Sarlah. Palladium-Catalyzed Cross-Coupling Reactions in Total Synthesis. Angewandte Chemie International Edition 2005, 44 (29) , 4442-4489. https://doi.org/10.1002/anie.200500368
- Lidia Feliu, Marta Planas. Cyclic Peptides Containing Biaryl and Biaryl Ether Linkages. International Journal of Peptide Research and Therapeutics 2005, 11 (1) , 53-97. https://doi.org/10.1007/s10989-004-1723-1
- Casey C. McComas, Brendan M. Crowley, Inkyu Hwang, Dale L. Boger. Synthesis and evaluation of methyl ether derivatives of the vancomycin, teicoplanin, and ristocetin aglycon methyl esters. Bioorganic & Medicinal Chemistry Letters 2003, 13 (17) , 2933-2936. https://doi.org/10.1016/S0960-894X(03)00513-4
- Pierre Cristau, Jean-Pierre Vors, Jieping Zhu. Rapid and diverse route to natural product-like biaryl ether containing macrocycles. Tetrahedron 2003, 59 (40) , 7859-7870. https://doi.org/10.1016/j.tet.2003.08.031
- John S. Davies. The cyclization of peptides and depsipeptides. Journal of Peptide Science 2003, 9 (8) , 471-501. https://doi.org/10.1002/psc.491
- Paul J. Krenitsky, Dale L. Boger. Synthesis of the (S,S,S)-diastereomer of the 15-membered biaryl ring system of RP 66453. Tetrahedron Letters 2003, 44 (21) , 4019-4022. https://doi.org/10.1016/S0040-4039(03)00856-6
- Jutta Wanner, Datong Tang, Casey C McComas, Brendan M Crowley, Wanlong Jiang, Jason Moss, Dale L Boger. A new and improved method for deglycosidation of glycopeptide antibiotics exemplified with vancomycin, ristocetin, and ramoplanin. Bioorganic & Medicinal Chemistry Letters 2003, 13 (6) , 1169-1173. https://doi.org/10.1016/S0960-894X(03)00051-9
- Lars H. Thoresen, Kevin Burgess. Total Syntheses of Vancomycin. 2003,,, 297-306. https://doi.org/10.1002/9783527620784.ch27d
- J.Jeffrey McAtee, Steven L Castle, Qing Jin, Dale L Boger. Synthesis and evaluation of vancomycin and vancomycin aglycon analogues that bear modifications in the residue 3 asparagine. Bioorganic & Medicinal Chemistry Letters 2002, 12 (9) , 1319-1322. https://doi.org/10.1016/S0960-894X(02)00130-0
- K. C. Nicolaou, Suk Young Cho, Robert Hughes, Nicolas Winssinger, Christian Smethurst, Harald Labischinski, Rainer Endermann. Solid- and Solution-Phase Synthesis of Vancomycin and Vancomycin Analogues with Activity against Vancomycin-Resistant Bacteria. Chemistry - A European Journal 2001, 7 (17) , 3798-3823. https://doi.org/10.1002/1521-3765(20010903)7:17<3798::AID-CHEM3798>3.0.CO;2-6
- Dale L. Boger. Vancomycin, teicoplanin, and ramoplanin: Synthetic and mechanistic studies. Medicinal Research Reviews 2001, 21 (5) , 356-381. https://doi.org/10.1002/med.1014
- Dale L. Boger, Seong Heon Kim, Yoshiki Mori, Jian-Hui Weng, Olivier Rogel, Steven L. Castle, J. Jeffrey McAtee. First and Second Generation Total Synthesis of the Teicoplanin Aglycon. Journal of the American Chemical Society 2001, 123 (9) , 1862-1871. https://doi.org/10.1021/ja003835i



