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Journal articles on the topic 'Total Synthesis, Antibiotics'

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Author: Grafiati

Published: 10 December 2022

Last updated: 28 January 2023

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1

Yosiiii, Eiichi, and Tadashi KOMETANI. "Total synthesis of pyranonaphthoquinone antibiotics." Journal of Synthetic Organic Chemistry, Japan 44, no. 10 (1986): 918–29. http://dx.doi.org/10.5059/yukigoseikyokaishi.44.918.

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2

KUBO, Akinori, and Naoki SAITO. "Total synthesis of isoquinolinequinone antibiotics." Journal of Synthetic Organic Chemistry, Japan 46, no. 2 (1988): 121–33. http://dx.doi.org/10.5059/yukigoseikyokaishi.46.121.

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3

LARSEN, D., M. OSHEA, and S. BROOKER. "Total synthesis of angucylinone antibiotics." Drug Discovery Today 1, no. 4 (April 1996): 172. http://dx.doi.org/10.1016/1359-6446(96)89074-x.

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4

USUI, TAKAYUKI, and SUMIO UMEZAWA. "Total synthesis of neomycin B." Journal of Antibiotics 40, no. 10 (1987): 1464–67. http://dx.doi.org/10.7164/antibiotics.40.1464.

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5

Andrade, Rodrigo. "Total Synthesis of Desmethyl Macrolide Antibiotics." Synlett 26, no. 16 (September 3, 2015): 2199–215. http://dx.doi.org/10.1055/s-0034-1381047.

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6

MAKITA, ATSUSHI, YASUHIRO YAMADA, and HIROSUKE OKADA. "The total synthesis of (.+-.)-patulolide A." Journal of Antibiotics 39, no. 9 (1986): 1257–62. http://dx.doi.org/10.7164/antibiotics.39.1257.

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7

Tatsuta, Kuniaki. "Total synthesis of the big four antibiotics and related antibiotics." Journal of Antibiotics 66, no. 3 (March 2013): 107–29. http://dx.doi.org/10.1038/ja.2012.126.

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8

YASUDA, NOBUYOSHI, KEIJI MATSUDA, HIDEO TSUTSUMI, and TAKAO TAKAYA. "Total synthesis of 3-O-demethylsporaricin A." Journal of Antibiotics 38, no. 11 (1985): 1512–25. http://dx.doi.org/10.7164/antibiotics.38.1512.

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9

ISSHIKI, KUNIO, YOSHIKAZU TAKAHASHI, TSUTOMU SAWA, HIROSHI NAGANAWA, TOMIO TAKEUCHI, HAMAO UMEZAWA, and KUNIAKI TATSUTA. "Total synthesis of indisocin and N-methylindisocin." Journal of Antibiotics 40, no. 8 (1987): 1202–3. http://dx.doi.org/10.7164/antibiotics.40.1202.

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10

TATSUTA, KUNIAKI, MASAAKI TAKAHASHI, and NOBORU TANAKA. "The First Total Synthesis of Pyralomicin 1c." Journal of Antibiotics 53, no. 1 (2000): 88–91. http://dx.doi.org/10.7164/antibiotics.53.88.

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11

Tavares, Francis, Jon P. Lawson, and A. I. Meyers. "Total Synthesis of Streptogramin Antibiotics. (−)-Madumycin II." Journal of the American Chemical Society 118, no. 13 (January 1996): 3303–4. http://dx.doi.org/10.1021/ja954312r.

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12

Suzuki, K. "Total synthesis of aryl C-glycoside antibiotics." Pure and Applied Chemistry 66, no. 10-11 (January 1, 1994): 2175–78. http://dx.doi.org/10.1351/pac199466102175.

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13

TATSUTA, K. "ChemInform Abstract: Total Synthesis of Macrolide Antibiotics." ChemInform 22, no. 19 (August 23, 2010): no. http://dx.doi.org/10.1002/chin.199119312.

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14

YONEMITSU, O., and K. HORITA. "ChemInform Abstract: Total Synthesis of Polyether Antibiotics." ChemInform 22, no. 19 (August 23, 2010): no. http://dx.doi.org/10.1002/chin.199119319.

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15

Nicolaou, K. C., Bin Zou, Dattatraya H. Dethe, Dong Bo Li, and David Y. K. Chen. "Total Synthesis of Antibiotics GE2270A and GE2270T." Angewandte Chemie 118, no. 46 (November 27, 2006): 7950–56. http://dx.doi.org/10.1002/ange.200602798.

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16

Nicolaou, K. C., Bin Zou, Dattatraya H. Dethe, Dong Bo Li, and David Y. K. Chen. "Total Synthesis of Antibiotics GE2270A and GE2270T." Angewandte Chemie International Edition 45, no. 46 (November 27, 2006): 7786–92. http://dx.doi.org/10.1002/anie.200602798.

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17

TATSUTA, KUNIAKI, TAKAYUKI INUKAI, SAYAKA ITOH, MASATAKA KAWARASAKI, and YUKO NAKANO. "Total Synthesis of a Tetracyclic Anti-tumor, UCE6." Journal of Antibiotics 55, no. 12 (2002): 1076–80. http://dx.doi.org/10.7164/antibiotics.55.1076.

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18

Essig, Sebastian, and Dirk Menche. "Stereochemistry and total synthesis of complex myxobacterial macrolides." Pure and Applied Chemistry 85, no. 6 (March 15, 2013): 1103–20. http://dx.doi.org/10.1351/pac-con-12-09-12.

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Polyketides are a very diverse family of natural products with an extremely broad range of biological activities and pharmacological properties, including antiproliferative, antibiotic, antifungal, or antiplasmodial activities, and in many cases specific targets are addressed at the molecular level. Their structures are characterized by diverse assemblies of methyl- and hydroxyl-bearing stereogenic centers enabling large numbers of stereochemical permutations, which are often embedded into macrolide rings. This complexity renders the stereochemical assignment and directed total synthesis challenging tasks. Within this review, we will detail practicable approaches for the stereochemical determination of diverse complex polyketides of myxobacterial origin by using computational and NMR methods in combination with novel procedures based on bioinformatics. Furthermore, we have developed efficient preparative strategies for the synthesis of these compounds, which have culminated in several first total syntheses. Key aspects of these various endeavors, which will also focus on the importance of conformational bias in complex polyketide analysis and synthesis, will be discussed within this review in the realm of the potent macrolide antibiotics etnangien and rhizopodin. Along these lines, we will also summarize novel methods for the rapid assembly of key structural elements of polyketides including a novel domino concept relying on a combination of a nucleophilic addition and a Tsuji–Trost reaction.

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19

TATSUTA, KUNIAKI, HIDEKAZU OZEKI, MAMI YAMAGUCHI, MASASHI TANAKA, TOSHIHARU OKUI, and MASAYA NAKATA. "Total synthesis and biological evaluation of unnatural (-)-medermycin ((-)-lactoquinomycin)." Journal of Antibiotics 44, no. 8 (1991): 901–2. http://dx.doi.org/10.7164/antibiotics.44.901.

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20

Tatsuta, Kuniaki. "ChemInform Abstract: Total Synthesis of the Big Four Antibiotics and Related Antibiotics." ChemInform 44, no. 27 (June 13, 2013): no. http://dx.doi.org/10.1002/chin.201327229.

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21

Kang, Han-Young. "Total Synthesis of Pikromycin and Related Macrolide Antibiotics." Rapid Communication in Photoscience 1, no. 2 (June 1, 2012): 59. http://dx.doi.org/10.5857/rcp.2012.1.2.059.

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22

Newman, David J. "Novel Modifications of Glycopeptide Antibiotics via Total Synthesis." ACS Medicinal Chemistry Letters 9, no. 2 (January 26, 2018): 66–67. http://dx.doi.org/10.1021/acsmedchemlett.8b00029.

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23

Tatsuta, Kuniaki, and Manabu Itoh. "Total synthesis of chlorinated phenylpyrrole antibiotics, (+)- and (−)-neopyrrolomycins." Tetrahedron Letters 34, no. 52 (January 1993): 8443–44. http://dx.doi.org/10.1016/s0040-4039(00)61354-0.

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24

Tatsuta, Kuniaki, and Manabu Itoh. "Total Synthesis of (+)- and (−)-Neopyrrolomycins, Chlorinated Phenylpyrrole Antibiotics." Bulletin of the Chemical Society of Japan 67, no. 5 (May 1994): 1449–55. http://dx.doi.org/10.1246/bcsj.67.1449.

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25

Andrade, Rodrigo B. "ChemInform Abstract: Total Synthesis of Desmethyl Macrolide Antibiotics." ChemInform 46, no. 48 (November 12, 2015): no. http://dx.doi.org/10.1002/chin.201548232.

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26

TATSUTA, KUNIAKI, TOMOKAZU HIRABAYASHI, MASAZUMI KOJIMA, YOSHIKAZU SUZUKI, and TAKASHI OGURA. "The First Total Synthesis of a Pyranonaphthoquinone Antitumor, BE-54238B." Journal of Antibiotics 57, no. 4 (2004): 291–97. http://dx.doi.org/10.7164/antibiotics.57.291.

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27

TATSUTA, KUNIAKI, and NAOYUKI MASUDA. "The First Total Synthesis of Natural (+)-Terpestacin, Syncytium Formation Inhibitor." Journal of Antibiotics 51, no. 6 (1998): 602–6. http://dx.doi.org/10.7164/antibiotics.51.602.

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28

TAMAKI, KAZUHIKO, AKI MATSUBARA, KAZUHIKO TANZAWA, and YUKIO SUGIMURA. "Total Synthesis and Inhibitory Activity against Gelatinase B of YL 01869P." Journal of Antibiotics 48, no. 1 (1995): 87–88. http://dx.doi.org/10.7164/antibiotics.48.87.

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29

TATSUTA, KUNIAKI, TAKUJI YOSHIMOTO, and HIROKI GUNJI. "Total Synthesis of MS-444, a Myosin Light Chain Kinase Inhibitor." Journal of Antibiotics 50, no. 3 (1997): 289–90. http://dx.doi.org/10.7164/antibiotics.50.289.

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30

Chen, Delin, Hoi Yee Chow, Kathy Hiu Laam Po, Wenjie Ma, Emily Lok Yee Leung, Zhenquan Sun, Ming Liu, Sheng Chen, and Xuechen Li. "Total Synthesis and Structural Establishment/Revision of Antibiotics A54145." Organic Letters 21, no. 14 (July 2, 2019): 5639–44. http://dx.doi.org/10.1021/acs.orglett.9b01972.

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31

Prusov, Evgeny V. "Total synthesis of antibiotics: recent achievements, limitations, and perspectives." Applied Microbiology and Biotechnology 97, no. 7 (February 23, 2013): 2773–95. http://dx.doi.org/10.1007/s00253-013-4757-5.

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32

Fu, Jiqiang, Stephane Laval, and Biao Yu. "Total Synthesis of Nucleoside Antibiotics Plicacetin and Streptcytosine A." Journal of Organic Chemistry 83, no. 13 (February 13, 2018): 7076–84. http://dx.doi.org/10.1021/acs.joc.8b00006.

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33

Nicolaou, K. C., Dattatraya H Dethe, Gulice Y C. Leung, Bin Zou, and David Y K. Chen. "Total Synthesis of Thiopeptide Antibiotics GE2270A, GE2270T, and GE2270C1." Chemistry - An Asian Journal 3, no. 2 (February 1, 2008): 413–29. http://dx.doi.org/10.1002/asia.200700361.

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34

Krohn, Karsten, and Jürgen Vitz. "Total Synthesis of Premithramycinone H and Related Anthrapyran Antibiotics." European Journal of Organic Chemistry 2004, no. 1 (January 2004): 209–19. http://dx.doi.org/10.1002/ejoc.200300451.

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35

SUZUKI, K., and T. MATSUMOTO. "ChemInform Abstract: Total Synthesis of Aryl C-Glycoside Antibiotics." ChemInform 25, no. 34 (August 19, 2010): no. http://dx.doi.org/10.1002/chin.199434299.

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36

SUZUKI, K. "ChemInform Abstract: Total Synthesis of Aryl C-Glycoside Antibiotics." ChemInform 26, no. 7 (August 18, 2010): no. http://dx.doi.org/10.1002/chin.199507317.

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37

TATSUTA, KUNIAKI, MASAAKI TAKAHASHI, NOBORU TANAKA, and KEN CHIKAUCHI. "Novel Synthesis of (+)-4-Acetoxy-3-hydroxyethyl-2-azetidinone from Carbohydrate. A Formal Total Synthesis of (+)-Thiehamycin." Journal of Antibiotics 53, no. 10 (2000): 1231–34. http://dx.doi.org/10.7164/antibiotics.53.1231.

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38

Senapati, Bidyut Kumar. "Progress in the total synthesis of inthomycins." Beilstein Journal of Organic Chemistry 17 (January 7, 2021): 58–82. http://dx.doi.org/10.3762/bjoc.17.7.

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The inthomycin family of antibiotics, isolated from Streptomyces strains, are interesting molecules for synthesis due to their characteristic common oxazole polyene chiral allylic β-hydroxycarbonyl fragments and significant biological activities. The full structural motif of the inthomycins is found in several more complex natural products including the oxazolomycins, 16-methyloxazolomycin, curromycins A and B, and KSM-2690. This review summarises the application of various efforts towards the synthesis of inthomycins and their analogues systematically.

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39

TATSUTA, KUNIAKI, HANA MISAWA, and KEN CHIKAUCHI. "Biomimetic Total Synthesis of Quinolactacin B, TNF Production Inhibitor, and Its Analogs." Journal of Antibiotics 54, no. 1 (2001): 109–12. http://dx.doi.org/10.7164/antibiotics.54.109.

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40

NAKAMURA, KAZUHIKO, TAKASHI KIMURA, HISASHI KANNO, and EISAKU TAKAHASHI. "Total Synthesis of (.+-.)-Phosphonothrixin, a Novel Herbicidal Antibiotic Containing C-P Bond." Journal of Antibiotics 48, no. 10 (1995): 1134–37. http://dx.doi.org/10.7164/antibiotics.48.1134.

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41

Tao, Shunan, Yang Wang, Ran Hong, and Sha-Hua Huang. "Potent Antibiotic Lemonomycin: A Glimpse of Its Discovery, Origin, and Chemical Synthesis." Molecules 27, no. 13 (July 5, 2022): 4324. http://dx.doi.org/10.3390/molecules27134324.

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Lemonomycin (1) was first isolated from the fermentation broth of Streptomyces candidus in 1964. The complete chemical structure was not elucidated until 2000 with extensive spectroscopic analysis. Lemonomycin is currently known as the only glycosylated tetrahydroisoquinoline antibiotic. Its potent antibacterial activity against Staphylococcus aureus and Bacillus subtilis and complex architecture make it an ideal target for total synthesis. In this short review, we summarize the research status of lemonomycin for biological activity, biosynthesis, and chemical synthesis. The unique deoxy aminosugar-lemonose was proposed to play a crucial role in biological activity, as shown in other antibiotics, such as arimetamycin A, nocathiacin I, glycothiohexide α, and thiazamycins. Given the self-resistance of the original bacterial host, the integration of biosynthesis and chemical synthesis to pursue efficient synthesis and further derivatization is in high demand for the development of novel antibiotics to combat antibiotic-resistant infections.

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42

Evans, David A., Scott J. Miller, and Michael D. Ennis. "Asymmetric synthesis of the benzoquinoid ansamycin antitumor antibiotics: total synthesis of (+)-macbecin." Journal of Organic Chemistry 58, no. 2 (January 1993): 471–85. http://dx.doi.org/10.1021/jo00054a035.

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43

KANAI, FUMIAKI, KUNIO ISSHIKI, YOJI UMEZAWA, HAJIME MORISHIMA, HIROSHI NAGANAWA, TOMOHISA TAKITA, TOMIO TAKEUCHI, and HAMAO UMEZAWA. "Vanoxonin, a new inhibitor of thymidylate synthetase. II. Structure determination and total synthesis." Journal of Antibiotics 38, no. 1 (1985): 31–38. http://dx.doi.org/10.7164/antibiotics.38.31.

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44

TSUCHIDA, TOSHIO, ASAKO KURODA, HAZUKI NAGAI, MASASHI YOSHIDA, TAKASHI NAKASHIMA, KANAME KONUKI, KUNIO ISSHIKI, HIKARU NAKAMURA, and TOMIO TAKEUCHI. "Convenient Total Synthesis of NM-3, an Antiangiogenesis Agent, and Its Optical Resolution." Journal of Antibiotics 56, no. 1 (2003): 38–41. http://dx.doi.org/10.7164/antibiotics.56.38.

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45

TATSUTA, KUNIAKI, FUMIE NARAZAKI, NOBUSUKE KASHIKI, JUN-ICHIRO YAMAMOTO, and SATOSHI NAKANO. "The First Total Synthesis of Cochleamycin A and Determination of the Absolute Structure." Journal of Antibiotics 56, no. 6 (2003): 584–90. http://dx.doi.org/10.7164/antibiotics.56.584.

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46

TATSUTA, KUNIAKI, SATOKO TAKANO, YUICHI IKEDA, SATOSHI NAKANO, and SHOJIRO MIYAZAKI. "The Total Synthesis and Absolute Structure of Antifungal Antibiotics (-)-PF 1163A and B." Journal of Antibiotics 52, no. 12 (1999): 1146–51. http://dx.doi.org/10.7164/antibiotics.52.1146.

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47

Yang, Hongzhi, Xue Liu, Qingong Li, Longbo Li, Jing-Ren Zhang, and Yefeng Tang. "Total synthesis and preliminary SAR study of (±)-merochlorins A and B." Organic & Biomolecular Chemistry 14, no. 1 (2016): 198–205. http://dx.doi.org/10.1039/c5ob01946j.

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48

Zhou, Yuxin, and Xiao-Wei Liang. "Recent applications of solid-phase strategy in total synthesis of antibiotics." RSC Advances 11, no. 60 (2021): 37942–51. http://dx.doi.org/10.1039/d1ra07503a.

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The recent applications of solid-phase strategy in total synthesis of antibiotics were summarized, and the structure–activity relationship could be established to conquer the challenge of bacterial resistance preparedness.

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49

Chida, Noritaka. "Total Synthesis of Nucleoside Antibiotics Possessing Novel N-Glycoside Structures." Journal of Synthetic Organic Chemistry, Japan 66, no. 11 (2008): 1105–15. http://dx.doi.org/10.5059/yukigoseikyokaishi.66.1105.

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50

Entwistle, David A. "Total Synthesis of Oxazole-Based Virginiamycin Antibiotics: 14,15-Anhydropristinamycin IIB." Synthesis 1998, S1 (March 1998): 603–12. http://dx.doi.org/10.1055/s-1998-5935.

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