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Journal articles on the topic 'Total Synthesis, Methodology'

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Author: Grafiati

Published: 6 September 2023

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1

Petrovčič, Jan, Chad Nicholas Ungarean, and David Sarlah. "Recent Chemical Methodology Advances in the Total Synthesis of Meroterpenoids." Acta Chimica Slovenica 68, no. 2 (June 15, 2021): 247–67. http://dx.doi.org/10.17344/acsi.2021.6921.

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Heterogeneity of meroterpenoids arising from their dual biosynthetic origins is constantly provoking synthetic chemists to utilize their ingenuity and revise their retrosynthetic logic. By studying recent publications on meroterpenoid synthesis,tremendous advances in the field of synthetic organic chemistry can be witnessed. This feature article covers some of the most intriguing total syntheses and synthetic studies towards the meroterpenoid class of natural products from the last five years.

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2

Isobe, Minoru, and Akinari Hamajima. "Ciguatoxin: developing the methodology for total synthesis." Natural Product Reports 27, no. 8 (2010): 1204. http://dx.doi.org/10.1039/b919467n.

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3

Umezawa, Taiki, and Fuyuhiko Matsuda. "Recent progress toward synthesis of chlorosulfolipids: total synthesis and methodology." Tetrahedron Letters 55, no. 19 (May 2014): 3003–12. http://dx.doi.org/10.1016/j.tetlet.2014.03.082.

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4

Williams, Craig, and Rebecca Pouwer. "Method in the Madness - Methodology from Total Synthesis." Synlett 23, no. 10 (May 29, 2012): 1446–58. http://dx.doi.org/10.1055/s-0031-1290967.

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5

Vedejs, Edwin, and Chutima Kongkittingam. "A Total Synthesis of (−)-Hemiasterlin UsingN-Bts Methodology." Journal of Organic Chemistry 66, no. 22 (November 2001): 7355–64. http://dx.doi.org/10.1021/jo0104882.

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6

Keck, Gary E., Eugene P. Boden, and Michael R. Wiley. "Total synthesis of (+)-colletodiol: new methodology for the synthesis of macrolactones." Journal of Organic Chemistry 54, no. 4 (February 1989): 896–906. http://dx.doi.org/10.1021/jo00265a033.

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7

Umezawa, Taiki, and Fuyuhiko Matsuda. "ChemInform Abstract: Recent Progress Toward Synthesis of Chlorosulfolipids: Total Synthesis and Methodology." ChemInform 45, no. 29 (July 3, 2014): no. http://dx.doi.org/10.1002/chin.201429265.

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8

Yeung, Kay, Rory C. Mykura, and Varinder K. Aggarwal. "Lithiation–borylation methodology in the total synthesis of natural products." Nature Synthesis 1, no. 2 (February 2022): 117–26. http://dx.doi.org/10.1038/s44160-021-00012-1.

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9

Xiang, Alan X., Donald A. Watson, Taotao Ling, and Emmanuel A. Theodorakis. "Total Synthesis of Clerocidin via a Novel, Enantioselective Homoallenylboration Methodology." Journal of Organic Chemistry 63, no. 20 (October 1998): 6774–75. http://dx.doi.org/10.1021/jo981331l.

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10

Johnstone, Craig, William J. Kerr, and Udo Lange. "Total synthesis of (+)-taylorione utilising modified Pauson–Khand reaction methodology." J. Chem. Soc., Chem. Commun., no. 4 (1995): 457–58. http://dx.doi.org/10.1039/c39950000457.

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11

Pouwer, Rebecca H., and Craig M. Williams. "ChemInform Abstract: Method in the Madness - Methodology from Total Synthesis." ChemInform 43, no. 35 (August 2, 2012): no. http://dx.doi.org/10.1002/chin.201235244.

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12

Baati, Rachid, John R. Falck, and Charles Mioskowski. "ChemInform Abstract: Chromium in Organic Synthesis. From Methodology to Total Synthesis of Natural Products." ChemInform 41, no. 1 (January 5, 2010): no. http://dx.doi.org/10.1002/chin.201001248.

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13

Vedejs, Edwin, and Chutima Kongkittingam. "ChemInform Abstract: A Total Synthesis of (-)-Hemiasterlin Using N-Bts Methodology." ChemInform 33, no. 15 (May 22, 2010): no. http://dx.doi.org/10.1002/chin.200215196.

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14

Enders, Dieter, Sylvie Dhulut, Daniel Steinbusch, and Audrey Herrbach. "Asymmetric Total Synthesis of (−)-Pironetin Employing the SAMP/RAMP Hydrazone Methodology." Chemistry - A European Journal 13, no. 14 (May 7, 2007): 3942–49. http://dx.doi.org/10.1002/chem.200601672.

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15

Nicolaou, K. C., Hui Li, Christopher N. C. Boddy, Joshi M. Ramanjulu, Tai-Yuen Yue, Swaminathan Natarajan, Xin-Jie Chu, Stefan Bräse, and Frank Rübsam. "Total Synthesis of Vancomycin—Part 1: Design and Development of Methodology." Chemistry - A European Journal 5, no. 9 (September 3, 1999): 2584–601. http://dx.doi.org/10.1002/(sici)1521-3765(19990903)5:9<2584::aid-chem2584>3.0.co;2-b.

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16

Katoh, Tadashi. "Enantioselective Total Synthesis of Otteliones A and B, Novel and Powerful Antitumor Agents from the Freshwater Plant Ottelia alismoides." Natural Product Communications 8, no. 7 (July 2013): 1934578X1300800. http://dx.doi.org/10.1177/1934578x1300800724.

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Otteliones A and B isolated from the freshwater plant Ottelia alismoides have attracted significant attention because of their potential as novel anticancer agents. In this review four independent enantioselective total syntheses and one formal synthesis of these natural products are presented with particular focus on their methodology and strategy.

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17

Fukuyama, Tohru. "Total Synthesis of Nitrogen-Containing Natural Products and Development of Synthetic Methodology." Journal of Synthetic Organic Chemistry, Japan 61, no. 6 (2003): 620–30. http://dx.doi.org/10.5059/yukigoseikyokaishi.61.620.

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18

Tarrade, Aurélie, Philippe Dauban, and Robert H. Dodd. "Enantiospecific Total Synthesis of (−)-Polyoxamic Acid Using 2,3-Aziridino-γ-lactone Methodology." Journal of Organic Chemistry 68, no. 24 (November 2003): 9521–24. http://dx.doi.org/10.1021/jo035039b.

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19

Wasserman, Harry H., and Rui Zhang. "Total synthesis of cyclotheonamides E2 and E3: application of cyano ylide methodology." Tetrahedron Letters 43, no. 20 (May 2002): 3743–46. http://dx.doi.org/10.1016/s0040-4039(02)00599-3.

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20

Faul, Margaret M., and Bret E. Huff. "Strategy and Methodology Development for the Total Synthesis of Polyether Ionophore Antibiotics†." Chemical Reviews 100, no. 6 (June 2000): 2407–74. http://dx.doi.org/10.1021/cr940210s.

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21

JOHNSTONE, C., W. J. KERR, and U. LANGE. "ChemInform Abstract: Total Synthesis of (+)-Taylorione Utilizing Modified Pauson-Khand Reaction Methodology." ChemInform 26, no. 32 (August 17, 2010): no. http://dx.doi.org/10.1002/chin.199532188.

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22

Roche, Stéphane P, Sophie Faure, and David J Aitken. "Total Synthesis of Cyclotheonamide C using a Tandem Backbone-Extension-Coupling Methodology." Angewandte Chemie International Edition 47, no. 36 (August 25, 2008): 6840–42. http://dx.doi.org/10.1002/anie.200802005.

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23

Roche, Stéphane P, Sophie Faure, and David J Aitken. "Total Synthesis of Cyclotheonamide C using a Tandem Backbone-Extension-Coupling Methodology." Angewandte Chemie 120, no. 36 (July 25, 2008): 6946–48. http://dx.doi.org/10.1002/ange.200802005.

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24

XIANG, A. X., D. A. WATSON, T. LING, and E. A. THEODORAKIS. "ChemInform Abstract: Total Synthesis of Clerocidin via a Novel, Enantioselective Homoallenylboration Methodology." ChemInform 30, no. 7 (June 17, 2010): no. http://dx.doi.org/10.1002/chin.199907264.

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25

Anderson, Oren P., Anthony GM Barrett, Jeremy J. Edmunds, Shun-Ichiro Hachiya, James A. Hendrix, Kiyoshi Horita, James W. Malecha, Christopher J. Parkinson, and Andrew VanSickle. "Applications of crotyldiisopinocampheylboranes in synthesis: a formal total synthesis of (+)-calyculin A." Canadian Journal of Chemistry 79, no. 11 (November 1, 2001): 1562–92. http://dx.doi.org/10.1139/v01-133.

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The formal total synthesis of the marine metabolite (+)-calyculin A is reported. The key steps involve (i) the use of Brown allylboration chemistry to control the relative and absolute stereochemistry of homoallylic alcohol arrays, thus setting eight of the desired stereocenters; (ii) Stille coupling methodology in the construction of the cyano tetraene unit of the natural product; and (iii) a modified CornforthMeyers approach to the synthesis of the oxazole fragment.Key words: calyculin, marine natural product, phosphatase inhibitor, total synthesis, palladium catalyzed coupling reactions, allylboration reactions, aldol reactions, spiroketal, CornforthMeyers oxazole reaction.

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26

Elford, Tim G., Stefan Nave, Ravindra P. Sonawane, and Varinder K. Aggarwal. "Total Synthesis of (+)-Erogorgiaene Using Lithiation–Borylation Methodology, and Stereoselective Synthesis of Each of Its Diastereoisomers." Journal of the American Chemical Society 133, no. 42 (October 26, 2011): 16798–801. http://dx.doi.org/10.1021/ja207869f.

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27

Maity, Arindam, Avishek Roy, Mrinal Kanti Das, Subhadip De, Malay Naskar, and Alakesh Bisai. "Oxidative cyanation of 2-oxindoles: formal total synthesis of (±)-gliocladin C." Organic & Biomolecular Chemistry 18, no. 8 (2020): 1679–84. http://dx.doi.org/10.1039/c9ob02752a.

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Oxidative direct cyanations of 3-alkyl/aryl 2-oxindoles using Cyano-1,2-BenziodoXol-3(1H)-one (CBX) have been developed. This methodology has been used for the formal total synthesis of (±)-gliocladin C in a few steps.

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28

Kingsbury, Jason S., and E. J. Corey. "Enantioselective Total Synthesis of Isoedunol and β-Araneosene Featuring Unconventional Strategy and Methodology." Journal of the American Chemical Society 127, no. 40 (October 2005): 13813–15. http://dx.doi.org/10.1021/ja055137+.

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29

Srikrishna, A., T. Jagadeeswar Reddy, P. Praveen Kumar, and D. Vijaykumar. "A Methodology for Spirocyclopentannulation. Stereoselective Total Synthesis of (±)-Tochuinyl Acetate and (±)-Dihydrotochuinyl Acetate." Synlett 1996, no. 01 (January 1996): 67–68. http://dx.doi.org/10.1055/s-1996-5318.

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30

Vicario, Jose L., Andreas Job, Michael Wolberg, Michael Müller, and Dieter Enders. "Asymmetric Total Synthesis of (−)-Callystatin A Employing the SAMP/RAMP Hydrazone Alkylation Methodology." Organic Letters 4, no. 6 (March 2002): 1023–26. http://dx.doi.org/10.1021/ol0256116.

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31

Campbell, Andrew D., Richard J. K. Taylor, and Tony M. Raynham. "The total synthesis of (−)-α-kainic acid using titanium-mediated diene metallabicyclisation methodology." Chemical Communications, no. 3 (1999): 245–46. http://dx.doi.org/10.1039/a809598a.

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32

Wang, Qian, and Jie-Ping Zhu. "ChemInform Abstract: Total Synthesis of Natural Products and the Synergy with Synthetic Methodology." ChemInform 44, no. 23 (May 16, 2013): no. http://dx.doi.org/10.1002/chin.201323207.

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33

Weinreb, Steven M. "Development of methodology for amide oxidation and its application to total synthesis ofsecurinegaalkaloids." Journal of Heterocyclic Chemistry 33, no. 5 (September 1996): 1437–43. http://dx.doi.org/10.1002/jhet.5570330503.

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34

Dubasi, Narsimhaswamy, and Ravi Varala. "Studies towards the Total Synthesis of (+)-Discodermolide: Desymmetrization Approach." Caribbean Journal of Science and Technology 10, no. 01 (2022): 28–35. http://dx.doi.org/10.55434/cbi.2022.10105.

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A new synthetic strategy for the construction of C-1 to C-7 and C-8 to C-15 subunits of (+)-discodermolide, a highly potent anticancer natural product, is reported in which we have exploited desymmetrization approach to create six stereogenic centers at once and stigmatic elements of the successful methodology include elaboration of two advanced fragments from a common precursor

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35

Munda, Mintu, Sovan Niyogi, Kundan Shaw, Sourav Kundu, Rhituparna Nandi, and Alakesh Bisai. "Electrocatalysis as a key strategy for the total synthesis of natural products." Organic & Biomolecular Chemistry 20, no. 4 (2022): 727–48. http://dx.doi.org/10.1039/d1ob02115j.

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36

Gueyrard, David. "Extension of the Modified Julia Olefination on Carboxylic Acid Derivatives: Scope and Applications." Synlett 29, no. 01 (October 16, 2017): 34–45. http://dx.doi.org/10.1055/s-0036-1590916.

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This account relates our work in the field of modified Julia olefination to extend this very useful olefination method to carboxylic acid derivatives. Since our preliminary results on lactones in 2005, the reaction has been extended to a large range of derivatives (lactams, imides and anhydrides) through an intra- or intermolecular process leading to a great variety of structures (enol ethers, enamides and exo enol esters). This article will also focus on the application of this methodology for the preparation of biologically interesting compounds and/or total syntheses of natural products such as C-disaccharide, bistramide A, jaspine B and maculalactone B.1 Introduction2 Modified Julia Olefination on Lactones2.1 Methylene Enol Ether Synthesis2.2 Substituted Enol Ether Synthesis2.3 Monofluorinated Enol Ether Synthesis2.4 Difluorinated Enol Ether Synthesis3 Applications3.1 Spiroketal Synthesis3.2 Spirocompound Synthesis3.3 Pseudodisaccharide Synthesis3.4 Total Synthesis of Jaspine B4 Modified Julia Olefination on Other Carboxylic Acid Derivatives4.1 Lactam Olefination and Spiroaminal Synthesis4.2 Bicyclic Enamide Synthesis by Intramolecular Modified Julia Olefination on Imides4.3 Modified Julia Olefination on Anhydrides5 Conclusion

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37

Corey, E. J., and Michael A. Letavic. "Enantioselective Total Synthesis of Gracilins B and C Using Catalytic Asymmetric Diels-Alder Methodology." Journal of the American Chemical Society 117, no. 37 (September 1995): 9616–17. http://dx.doi.org/10.1021/ja00142a051.

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38

Heathcock, Clayton H., and Stephen H. Montgomery. "Acyclic stereoselection. 28. Use of stereoselective aldol methodology in the total synthesis of cladinose." Tetrahedron Letters 26, no. 8 (January 1985): 1001–4. http://dx.doi.org/10.1016/s0040-4039(00)98496-x.

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39

Gareau, Yves, Robert Zamboni, and Alexander W. Wong. "Total synthesis of N-methyl LTC4: a novel methodology for the monomethylation of amines." Journal of Organic Chemistry 58, no. 6 (March 1993): 1582–85. http://dx.doi.org/10.1021/jo00058a049.

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40

Faul, Margaret M., and Bret E. Huff. "ChemInform Abstract: Strategy and Methodology Development for the Total Synthesis of Polyether Ionorephore Antibiotics." ChemInform 31, no. 34 (June 3, 2010): no. http://dx.doi.org/10.1002/chin.200034265.

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41

Wasserman, Harry H., and Rui Zhang. "ChemInform Abstract: Total Synthesis of Cyclotheonamides E2 and E3: Application of Cyano Ylide Methodology." ChemInform 33, no. 36 (May 20, 2010): no. http://dx.doi.org/10.1002/chin.200236189.

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42

Hashimoto, Hajime, Shinnosuke Wakamori, Kazutada Ikeuchi, and Hidetoshi Yamada. "Divergent Synthesis of Four Monomeric Ellagitannins toward the Total Synthesis of an Oligomeric Ellagitannin, Nobotanin K." Organics 3, no. 3 (September 6, 2022): 293–303. http://dx.doi.org/10.3390/org3030022.

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Oligomeric ellagitannins are challenging synthetic targets due to the need for an abundant supply of their composed monomeric ellagitannins and a synthetic methodology to connect them. This work focused on the divergent synthesis of the four monomeric ellagitannins from a common intermediate as a step toward the total synthesis of nobotanin K, a class of compounds that includes oligomeric ellagitannins and were isolated in plants belonging to the Melastomataceae family. Implementing our method, the four natural products could be easily supplied, suggesting that through this novel route, the total synthesis of nobotanin K could be achieved smoothly.

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43

Zhu, Bin, and James S. Panek. "Methodology Based on Chiral Silanes in the Synthesis of Polypropionate-Derived Natural Products − Total Synthesis of Epothilone A." European Journal of Organic Chemistry 2001, no. 9 (May 2001): 1701–14. http://dx.doi.org/10.1002/1099-0690(200105)2001:9<1701::aid-ejoc1701>3.0.co;2-#.

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44

Roesner, Stefan, and Varinder K. Aggarwal. "Enantioselective synthesis of (R)-tolterodine using lithiation/borylation–protodeboronation methodology." Canadian Journal of Chemistry 90, no. 11 (November 2012): 965–74. http://dx.doi.org/10.1139/v2012-069.

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The synthesis of the pharmaceutical (R)-tolterodine is reported using lithiation/borylation–protodeboronation of a homoallyl carbamate as the key step. This step was tested with two permutations: an electron-neutral aryl Li-carbamate reacting with an electron-rich boronic ester and an electron-rich aryl Li-carbamate reacting with an electron-neutral boronic ester. It was found that the latter arrangement was considerably better than the former. Further improvements were achieved using magnesium bromide in methanol leading to a process that gave high yield and high enantioselectivity in the lithiation/borylation reaction. The key step was used in an efficient synthesis of (R)-tolterodine in a total of eight steps in a 30% overall yield and 90% ee.

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45

Isoda, Yuta, Norihiko Sasaki, Kei Kitamura, Shuji Takahashi, Sujit Manmode, Naoko Takeda-Okuda, Jun-ichi Tamura, Toshiki Nokami, and Toshiyuki Itoh. "Total synthesis of TMG-chitotriomycin based on an automated electrochemical assembly of a disaccharide building block." Beilstein Journal of Organic Chemistry 13 (May 16, 2017): 919–24. http://dx.doi.org/10.3762/bjoc.13.93.

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The total synthesis of TMG-chitotriomycin using an automated electrochemical synthesizer for the assembly of carbohydrate building blocks is demonstrated. We have successfully prepared a precursor of TMG-chitotriomycin, which is a structurally-pure tetrasaccharide with typical protecting groups, through the methodology of automated electrochemical solution-phase synthesis developed by us. The synthesis of structurally well-defined TMG-chitotriomycin has been accomplished in 10-steps from a disaccharide building block.

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46

Lübken, Dennis, Marius Saxarra, and Markus Kalesse. "Tris(acetylacetonato) Iron(III): Recent Developments and Synthetic Applications." Synthesis 51, no. 01 (November 27, 2018): 161–77. http://dx.doi.org/10.1055/s-0037-1610393.

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Tris(acetylacetonato) iron(III) [Fe(acac)3] is an indispensable reagent in synthetic chemistry. Its applications range from hydrogen atom transfer to cross-coupling reactions and to use as a Lewis acid. Consequently, the exceptional utility of Fe(acac)3 has been demonstrated in several total syntheses. This short review summarizes the applications of Fe(acac)3 in methodology and catalysis and highlights its use for the synthesis of medicinally relevant structures and in natural product syntheses.1 Introduction2 Hydrogen Atom Transfer (HAT)3 Oxidations and Radical Transformations4 Synthesis and Use of Alkynes and Allenes5 Cross-Couplings and Cycloisomerizations6 Borylations7 Miscellaneous Reactions8 Conclusions

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47

Yao, Sulan, Mogens Johannsen, Rita G. Hazell, and Karl Anker Jørgensen. "Total Synthesis of (R)-Dihydroactinidiolide and (R)-Actinidiolide Using Asymmetric Catalytic Hetero-Diels−Alder Methodology." Journal of Organic Chemistry 63, no. 1 (January 1998): 118–21. http://dx.doi.org/10.1021/jo971528y.

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48

SRIKRISHNA, A., T. J. REDDY, P. P. KUMAR, and D. VIJAYKUMAR. "ChemInform Abstract: A Methodology for Spirocyclopentannulation. Stereoselective Total Synthesis of (.+-.)-Tochuinyl Acetate and (.+-.)-Dihydrotochuinyl Acetate." ChemInform 27, no. 19 (August 5, 2010): no. http://dx.doi.org/10.1002/chin.199619094.

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49

Campbell, Andrew D., Tony M. Raynham, and Richard J. K. Taylor. "ChemInform Abstract: The Total Synthesis of (-)-α-Kainic Acid Using Titanium-Mediated Diene Metallabicyclization Methodology." ChemInform 30, no. 22 (June 15, 2010): no. http://dx.doi.org/10.1002/chin.199922197.

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50

Vicario, Jose L., Andreas Job, Michael Wolberg, Michael Mueller, and Dieter Enders. "ChemInform Abstract: Asymmetric Total Synthesis of (-)-Callystatin A Employing the SAMP/RAMP Hydrazone Alkylation Methodology." ChemInform 33, no. 36 (May 20, 2010): no. http://dx.doi.org/10.1002/chin.200236220.

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