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P.; Taft, F.; Kirschning, A., The Interplay between Mutasynthesis and 72 (k) Hanari, T.; Shimada, N.; Kurosaki, Y.; Thrimurtulu, N.; Nambu,
Semisynthesis: Generation and Evaluation of an Ansamitocin Library. 73 H.; Anada, M.; Hashimoto, S., Asymmetric Total Synthesis of (–)‐
Angew. Chem. Int. Ed. 2012, 51 (3), 752‐757; (f) Just‐Baringo, X.; 74 Englerin
A through Catalytic Diastereo‐ and Enantioselective
Albericio, F.; Álvarez, M., Thiopeptide Engineering: A 75 Carbonyl Ylide Cycloaddition. Chem. Eur. J. 2015, 21 (33), 11671–11676;
Multidisciplinary Effort towards Future Drugs. Angew. Chem. Int. Ed. 76 (l) Nelson, R.; Gulías, M.; Mascareñas, J. L.; López, F., Concise,
2014, 53 (26), 6602‐6616.
77 Enantioselective, and Versatile Synthesis of (−)‐Englerin A Based on a
(4) (a) Jørgensen, L.; McKerrall, S. J.; Kuttruff, C. A.; Ungeheuer, F.; 78 Platinum‐Catalyzed [4C+ 3C] Cycloaddition of Allenedienes. Angew.
Felding, J.; Baran, P. S., 14‐Step Synthesis of (+)‐Ingenol from (+)‐3‐ 79 Chem. Int. Ed. 2016, 55 (46), 14359–14363; (m) Kusama, H.; Tazawa,
Carene. Science 2013, 341 (6148), 878–882; (b) Chen, K.; Baran, P. S., 80 A.; Ishida, K.; Iwasawa, N., Total Synthesis of (±)‐Englerin A Using An
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10 Total Synthesis of Eudesmane Terpenes by Site‐Selective C–H 81 Intermolecular [3+2] Cycloaddition Reaction of Platinum‐Containing
11 Oxidations. Nature 2009, 459, 824–828; (c) Wilde, N. C.; Isomura, M.; 82 Carbonyl Ylide. Chem. Asien. J. 2016, 11 (1), 64–67; (n) Liu, P.; Cui, Y.;
12 Mendoza, A.; Baran, P. S., Two‐Phase Synthesis of (−)‐Taxuyunnanine 83 Chen, K.; Zhou, X.; Pan, W.; Ren, J.; Wang, Z., Total Syntheses of (–
13 D. J. Am. Chem. Soc. 2014, 136 (13), 4909–4912; (d) Chu, H.; Smith, J. 84 )‐Englerins A/B, (+)‐Orientalols E/F, and (–)‐Oxyphyllol. Org. Lett.
14 M.; Felding, J.; Baran, P. S., Scalable Synthesis of (−)‐Thapsigargin. 85 2018, 20 (9), 2517–2521; (o) Guo, L.; Plietker, B., β‐Ketoesters as Mono‐
15 ACS Cent. Sci. 2017, 3 (1), 47–51; (e) Renata, H.; Zhou, Q.; Baran, P. S., 86 or Bisnucleophiles: A Concise Enantioselective Total Synthesis of (−)‐
16 Strategic Redox Relay Enables A Scalable Synthesis of Ouabagenin, A 87 Englerin A and B. Angew. Chem. Int. Ed. 2019, 58 (25), 8346–8350; (p)
17 Bioactive Cardenolide. Science 2013, 339 (6115), 59–63.
88 Reagan, C.; Trevitt, G.; Tchabanenko, K., Total Synthesis of (±)‐
18 (5) Malik, S.; Cusidó, R. M.; Mirjalili, M. H.; Moyano, E.; Palazón, J.; 89 Englerin A and Its Tuncated Analogues. Eur. J. Org. Chem. 2019, 2019
19 Bonfill, M., Production of the Anticancer Drug Taxol in Taxus baccata 90 (5), 1027–1037.
20 Suspension Cultures: A Review. Process Biochem. 2011, 46 (1), 23–34. 91 (11) (a) Xu, J.; Caro‐Diaz, E. J. E.; Theodorakis, E. A., Enantioselective
21 (6) (a) Paddon, C. J.; Westfall, P.; Pitera, D.; Benjamin, K.; Fisher, 92 Formal Synthesis of (–)‐Englerin
A via a Rh‐Catalyzed [4+3]
22 K.; McPhee, D.; Leavell, M.; Tai, A.; Main, A.; Eng, D., High‐Level 93 Cycloaddition Reaction. Org. Lett. 2010, 12 (16), 3708–3711; (b) Lee, J.;
23 Semisynthetic Production of the Potent Antimalarial Artemisinin. 94 Parker, K. A., A Formal Synthesis of (–)‐Englerin A by Relay Ring
24 Nature 2013, 496 (7446), 528–532; (b) Chaturvedi, D., Sesquiterpene 95 Closing Metathesis and Transannular Etherification. Org. Lett. 2012,
25 Lactones: A Versatile Class of Structurally Diverse Natural Products 96 14 (11), 2682–2685; (c) Gao, P.; Cook, S. P., A Reductive‐Heck Approach
26 and their Semisynthetic Analogs as Potential Antimalarials. In 97 to the Hydroazulene Ring System: A Formal Synthesis of the
27 Discovery and Development of Therapeutics from Natural Products 98 Englerins. Org. Lett. 2012, 14 (13), 3340–3343; (d) Morisaki, K.; Sasano,
28 Against Neglected Tropical Diseases, Brahmachari, G., Ed. Elsevier: 99 Y.; Koseki, T.; Shibuta, T.; Kanoh, N.; Chiou, W.‐H.; Iwabuchi, Y.,
29 2019; pp 49‐85.
100 Nazarov Cyclization Entry to Chiral Bicyclo5.3.0decanoid Building
30 (7) Nakagawa, A.; Matsumura, E.; Koyanagi, T.; Katayama, T.;101 Blocks and Its Application to Formal Synthesis of (–)‐Englerin A. Org.
31 Kawano, N.; Yoshimatsu, K.; Yamamoto, K.; Kumagai, H.; Sato, F.;102 Lett. 2017, 19 (19), 5142–5145; (e) Hagihara, S.; Hanaya, K.; Sugai, T.;
32 Minami, H., Total Biosynthesis of Opiates by Stepwise Fermentation103 Shoji, M., Formal Synthesis of Englerin A Utilizing Regio‐ and
33 using Engineered Escherichia coli. Nat. Commun. 2016, 7 (1), 10390. 104 Diastereoselective [4+3] Cycloaddition. J. Antibiot. 2018, 71 (2), 257–
34 (8) Ratnayake, R.; Covell, D.; Ransom, T. T.; Gustafson, K. R.; Beutler,105 262.
35 J. A., Englerin A, A Selective Inhibitor of Renal Cancer Cell Growth,106 (12) Burkhardt, I.; Siemon, T.; Henrot, M.; Studt, L.; Rösler, S.;
36 from Phyllanthus engleri. Org. Lett. 2009, 11 (1), 57–60.
107 Tudzynski, B.; Christmann, M.; Dickschat, J. S., Mechanistic
37 (9) (a) Akbulut, Y.; Gaunt, H. J.; Muraki, K.; Ludlow, M. J.; Amer, M.108 Characterisation of Two Sesquiterpene Cyclases from the Plant
38 S.; Bruns, A.; Vasudev, N. S.; Radtke, L.; Willot, M.; Hahn, S.; Seitz,109 Pathogenic Fungus Fusarium fujikuroi. Angew. Chem. Int. Ed. 2016, 55
39 T.; Ziegler, S.; Christmann, M.; Beech, D. J.; Waldmann, H., (–)‐110 (30), 8748–8751.
40 Englerin A is a Potent and Selective Activator of TRPC4 and TRPC5111 (13) Iwasawa, N.; Funahashi, M.; Narasaka, K., Total Synthesis of 10‐
41 Calcium Channels. Angew. Chem. Int. Ed. 2015, 54 (12), 3787–3791; (b)112 Isothiocyanatoguaia‐6‐ene. Chem. Lett. 1994, 23 (9), 1697‐1700.
42 Ludlow, M. J.; Gaunt, H. J.; Rubaiy, H. N.; Musialowski, K. E.; Blythe,113 (14) Bian, G.;
Deng, Z.; Liu, T., Strategies for Terpenoid
43 N. M.; Vasudev, N. S.; Muraki, K.; Beech, D. J., (–)‐Englerin A‐Evoked114 Overproduction and New Terpenoid Discovery. Curr. Opin.
44 Cytotoxicity Is Mediated by Na+ Influx and Counteracted by Na+/K+‐115 Biotechnol. 2017, 48, 234–241.
45 ATPase. J. Biol. Chem. 2017, 292 (2), 723–731.
116 (15) Zhu, F.; Zhong, X.; Hu, M.; Lu, L.; Deng, Z.; Liu, T., In Vitro
46 (10) (a) Willot, M.; Radtke, L.; Könning, D.; Fröhlich, R.; Gessner, V.117 Reconstitution of Mevalonate Pathway and Targeted Engineering of
47 H.; Strohmann, C.; Christmann, M., Total Synthesis and Absolute118 Farnesene Overproduction in Escherichia coli. Biotechnol. Bioeng.
48 Configuration of the Guaiane Sesquiterpene Englerin A. Angew.119 2014, 111 (7), 1396–1405.
49 Chem. Int. Ed. 2009, 48 (48), 9105–9108; (b) Radtke, L.; Willot, M.;120 (16) Bian, G.; Hou, A.; Yuan, Y.; Hu, B.; Cheng, S.; Ye, Z.; Di, Y.;
50 Sun, H.; Ziegler, S.; Sauerland, S.; Strohmann, C.; Fröhlich, R.;121 Deng, Z.; Liu, T., Metabolic Engineering‐Based Rapid
51 Habenberger, P.; Waldmann, H.; Christmann, M., Total Synthesis and122 Characterization of a Sesquiterpene Cyclase and the Skeletons of
52 Biological Evaluation of (–)‐Englerin A and B: Synthesis of Analogues123 Fusariumdiene and Fusagramineol from Fusarium graminearum. Org.
53 with Improved Activity Profile. Angew. Chem. Int. Ed. 2011, 50 (17),124 Lett. 2018, 20 (6), 1626–1629.
54 3998–4002; (c) Zhou, Q.; Chen, X.; Ma, D., Asymmetric, Protecting‐125 (17) Crossley, S. W.; Barabé, F.; Shenvi, R. A., Simple, Chemoselective,
55 Group‐Free Total Synthesis of (−)‐Englerin A. Angew. Chem. Int. Ed.126 Catalytic Olefin Isomerization. J. Am. Chem. Soc. 2014, 136 (48),
56 2010, 49 (20), 3513–3516; (d) Molawi, K.; Delpont, N.; Echavarren, A.127 16788–16791.
57 M., Enantioselective Synthesis of (−)‐Englerins A and B. Angew. Chem.128 (18) VanRheenen, V.; Kelly, R.; Cha, D. Y., An Improved Catalytic
58 Int. Ed. 2010, 49 (20), 3517–3519; (e) Nicolaou, K. C.; Kang, Q.; Ng, S.129 OsO4 Oxidation of Olefins to cis‐1, 2‐Glycols using Tertiary Amine
59 Y.; Chen, D. Y.‐K., Total Synthesis of Englerin A. J. Am. Chem. Soc.130 Oxides as the Oxidant. Tetrahedron Lett. 1976, 17 (23), 1973–1976.
60 2010, 132 (23), 8219–8222; (f) Li, Z.; Nakashige, M.; Chain, W. J., A Brief131 (19) Sharpless, K. B.; Amberg, W.; Bennani, Y. L.; Crispino, G. A.;
61 Synthesis of (–)‐Englerin A. J. Am. Chem. Soc. 2011, 133 (17), 6553–6556;132 Hartung, J.; Jeong, K. S.; Kwong, H. L.; Morikawa, K.; Wang, Z. M.,
62 (g) Takahashi, K.; Komine, K.; Yokoi, Y.; Ishihara, J.; Hatakeyama, S.,133 The Osmium‐Catalyzed Asymmetric Dihydroxylation: A New Ligand
63 Stereocontrolled Total Synthesis of (–)‐Englerin A. J. Org. Chem. 2012,134 Class and a Process Improvement. J. Org. Chem. 1992, 57 (10), 2768–
64 77 (17), 7364–7370; (h) Zahel, M.; Kessberg, A.; Metz, P., A Short135 2771.
65 Enantioselective Total Synthesis of (–)‐Englerin A. Angew. Chem. Int.136 (20) (a) Ferrer, M.; Gibert, M.; Sánchez‐Baeza, F.; Messeguer, A., Easy
66 Ed. 2013, 52 (20), 5390–5392; (i) Wang, J.; Chen, S.‐G.; Sun, B.‐F.; Lin,137 Availability of More Concentrated and Versatile Dimethyldioxirane
67 G.‐Q.; Shang, Y.‐J., Collective Total Synthesis of Englerin A and B,138 Solutions. Tetrahedron Lett. 1996, 37 (20), 3585–3586; (b) Murray, R.
68 Orientalol
E
and F, and Oxyphyllol: Application of the139 W.; Singh, M., Synthesis of Epoxides Using Dimethyldioxirane: trans‐
69 Organocatalytic [4+3] Cycloaddition Reaction. Chem. Eur. J. 2013, 19140 Stilbene Oxide. Org. Synth. 1997, 91.
70 (7), 2539–2547; (j) Zhang, J.; Zheng, S.; Peng, W.; Shen, Z., Total141 (21) Sutthivaiyakit, S.; Nakorn, N. N.; Kraus, W.; Sutthivaiyakit, P., A
71 Synthesis of (−)‐Englerin A. Tetrahedron Lett. 2014, 55 (7), 1339–1341;142 Novel 29‐nor‐3,4‐seco‐Friedelane Triterpene and a New Guaiane
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