Development of a Modular Synthetic Route to (+)-Pleuromutilin, (+)-12-epi-Mutilins, and Related Structures

Journal of the American Chemical Society

Volumn 139, Issue 45, 2017, Pages 16377-16388

  Zeng, Mingshuo ^a   Murphy, Stephen K ^a   Herzon, Seth B ^a,b  

^a YALE UNIVERSITY   (United States)

^b YALE UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL REACTIONS; CYANIDES; KETONES; ORGANOMETALLICS;

COUPLING REACTION; DIASTEREOMERIC; ENANTIOSELECTIVE; GLYCOLIC ACIDS; NOVEL ANTIBIOTICS; ORGANOLITHIUM REAGENT; REDUCTIVE CYCLIZATION; SYNTHETIC ROUTES;

CYCLIZATION;

11,12 DI EPI MUTILIN; 11,12 DI EPI PLEUROMUTILIN; 12 EPI MUTILIN; 12 EPI PLEUROMUTILIN; 2 CYCLOHEXENONE; ALDEHYDE DERIVATIVE; ALKENE; ALKYNYLALDEHYDE; BICARBONATE; CYCLOPENTENE DERIVATIVE; DI TERT BUTYLDICARBONATE; DIKETONE; GLYCOLIC ACID; HYDRINDANONE; INDANONE DERIVATIVE; IODIDE; LITHIUM DERIVATIVE; METHYLLITHIUM; NICKEL; NITRILE; ORGANOLITHIUM COMPOUND; PLEUROMUTILIN; PLEUROMUTILIN ANTIBIOTIC AGENT; UNCLASSIFIED DRUG; DITERPENE; KETONE; MUTILIN; POLYCYCLIC HYDROCARBON;

ACYLATION; ARTICLE; CATALYSIS; CYANATION; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOSELECTIVITY; EPIMERIZATION; SEQUENCE ANALYSIS; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION; CHEMISTRY; CONFORMATION; PLEUROTUS; STEREOISOMERISM; SYNTHESIS;

DITERPENES; KETONES; MOLECULAR CONFORMATION; PLEUROTUS; POLYCYCLIC COMPOUNDS; STEREOISOMERISM;

EID: 85034216303     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/jacs.7b09869     Document Type: Article

References (92)

1. Kavanagh, F.; Hervey, A.; Robbins, W. J. Proc. Natl. Acad. Sci. U. S. A. 1951, 37, 570 10.1073/pnas.37.9.570
2. Anchel, M. J. Biol. Chem. 1952, 199, 133
3. Arigoni, D. Gazz. Chim. Ital. 1962, 92, 884
4. Birch, A. J.; Holzapfel, C. W.; Rickards, R. W. Tetrahedron 1966, 22, 359 10.1016/S0040-4020(01)90949-4
5. Dobler, M.; Duerr, B. G. Cryst. Struct. Comm. 1975, 4, 259
6. Arigoni, D. Pure Appl. Chem. 1968, 17, 331 10.1351/pac196817030331
7. Schlunzen, F.; Pyetan, E.; Fucini, P.; Yonath, A.; Harms, J. M. Mol. Microbiol. 2004, 54, 1287 10.1111/j.1365-2958.2004.04346.x
8. Davidovich, C.; Bashan, A.; Auerbach-Nevo, T.; Yaggie, R. D.; Gontarek, R. R.; Yonath, A. Proc. Natl. Acad. Sci. U. S. A. 2007, 104, 4291 10.1073/pnas.0700041104
9. Egger, H.; Reinshagen, H. J. Antibiot. 1976, 29, 923 10.7164/antibiotics.29.923
10. For a review of synthetic and semisynthetic studies of (+)-pleuromutilin (1), see: Fazakerley, N. J.; Procter, D. J. Tetrahedron 2014, 70, 6911 10.1016/j.tet.2014.05.092
11. Daum, R. S.; Kar, S.; Kirkpatrick, P. Nat. Rev. Drug Discovery 2007, 6, 865 10.1038/nrd2442
12. Paukner, S.; Riedl, R. Cold Spring Harbor Perspect. Med. 2017, 7, a027110 10.1101/cshperspect.a027110
13. Walsh, C. T.; Wencewicz, T. A. J. Antibiot. 2014, 67, 7 10.1038/ja.2013.49
14. https://globenewswire.com/news-release/2017/09/18/1124000/0/en/Nabriva-Therapeutics-Announces-Positive-Topline-Results-from-Global-Phase-3-Clinical-Trial-Evaluating-IV-and-Oral-Lefamulin-for-the-Treatment-of-Community-Acquired-Bacterial-Pneumo.html accessed 10/09/2017.
15. Berner, H.; Vyplel, H.; Schulz, G.; Schneider, H. Monatsh. Chem. 1986, 117, 1073 10.1007/BF00811277
16. Paukner, S.; Gruss, A.; Fritsche, T. R.; Ivezic-Schoenfeld, Z.; Jones, R. N. In Vitro Activity of the Novel Pleuromutilin BC-3781 Tested Against Bacterial Pathogens Causing Sexually Transmitted Diseases (STD). In 53rd Interscience Conference on Antimicrobial Agents and Chemotherapy (ICAAC), Denver, CO, 2013.
17. Paukner, S.; Strickmann, D. B.; Ivezic-Schoenfeld, Z., Extended Spectrum Pleuromutilins: Mode-of-action Studies. In 24th European Congress of Clinical Microbiology and Infectious Diseases (ECCMID), Barcelona, Spain, 2014.
18. Wicha, W. W.; Ivezic-Schoenfeld, Z., In Vivo Activity of Extended Spectrum Pleuromutilins in Murine Sepsis Model. In 24th European Congress of Clinical Microbiology and Infectious Diseases (ECCMID), Barcelona, Spain, 2014.
19. Thirring, K.; Heilmayer, W.; Riedl, R.; Kollmann, H.; Ivezic-Schoenfeld, Z.; Wicha, W.; Paukner, S.; Strickmann, D. Preparation of 12-epi-pleuromutilin derivatives as antimicrobial agents. Patent WO2015110481A1, 2015.
20. Paukner, S.; Kollmann, H.; Riedl, R.; Ivezic-Schoenfeld, Z., Kill curves of the Novel Extended-Spectrum Pleuromutilin Antibiotic BC-9529. In 25th European Congress of Clinical Microbiology and Infectious Diseases (ECCMID), Copenhagen, Denmark, 2015.
21. Paukner, S.; Wicha, W. W.; Heilmayer, W.; Thirring, K.; Riedl, R., Extended Spectrum Pleuromutilins: Potent Translation Inhibitors with Broad-Spectrum Antibacterial Activity In Vitro and In Vivo. In Interscience Conference of Antimicrobial Agents and Chemotherapy/International Congress of Chemotherapy and Infection (ICAAC/ICC), San Diego, CA, 2015.
22. Paukner, S.; Wicha, W. W.; Thirring, K.; Kollmann, H.; Ivezic-Schoenfeld, Z., In Vitro and In Vivo Efficacy of Novel Extended Spectrum Pleuromutilins Against S. aureus and S. pneumoniae. In 25th European Congress of Clinical Microbiology and Infectious Diseases (ECCMID), Copenhagen, Denmark, 2015.
23. Wicha, W. W.; Paukner, S.; Strickmann, D. B.; Thirring, K.; Kollmann, H.; Heilmayer, W.; Ivezic-Schoenfeld, Z., Efficacy of Novel Extended Spectrum Pleuromutilins Against E. coli In Vitro and In Vivo. In 25th European Congress of Clinical Microbiology and Infectious Diseases (ECCMID), Copenhagen, Denmark, 2015.
24. https://www.cdc.gov/drugresistance/biggest-threats.html, accessed May 13, 2017.
25. Post, K. W.; Songer, J. G. Anaerobe 2004, 10, 47 10.1016/j.anaerobe.2004.01.003
26. Murphy, S. K.; Zeng, M.; Herzon, S. B. Org. Lett. 2016, 18, 4880 10.1021/acs.orglett.6b02320
27. Murphy, S. K.; Zeng, M.; Herzon, S. B. Science 2017, 356, 956 10.1126/science.aan0003
28. Murphy, S. K.; Zeng, M.; Herzon, S. B. Org. Lett. 2017, 19, 4980 10.1021/acs.orglett.7b02476
29. Page, M. G. P. Beta-Lactam Antibiotics. In Antibiotic Discovery and Development; Dougherty, T. J.; Pucci, M. J., Eds.; Springer: Amsterdam, 2012; pp 79-117.
30. Okano, A.; Isley, N. A.; Boger, D. L. Chem. Rev. 2017, 117, 11952 10.1021/acs.chemrev.6b00820
31. Liu, F.; Myers, A. G. Curr. Opin. Chem. Biol. 2016, 32, 48 10.1016/j.cbpa.2016.03.011
32. Seiple, I. B.; Zhang, Z.; Jakubec, P.; Langlois-Mercier, A.; Wright, P. M.; Hog, D. T.; Yabu, K.; Allu, S. R.; Fukuzaki, T.; Carlsen, P. N.; Kitamura, Y.; Zhou, X.; Condakes, M. L.; Szczypiński, F. T.; Green, W. D.; Myers, A. G. Nature 2016, 533, 338 10.1038/nature17967
33. For a review, see: Wright, P. M.; Seiple, I. B.; Myers, A. G. Angew. Chem., Int. Ed. 2014, 53, 8840 10.1002/anie.201310843
34. Gibbons, E. G. J. Am. Chem. Soc. 1982, 104, 1767 10.1021/ja00370a067
35. Boeckman, R. K.; Springer, D. M.; Alessi, T. R. J. Am. Chem. Soc. 1989, 111, 8284 10.1021/ja00203a043
36. Fazakerley, N. J.; Helm, M. D.; Procter, D. J. Chem.-Eur. J. 2013, 19, 6718 10.1002/chem.201300968
37. Kahn, M. Tetrahedron Lett. 1980, 21, 4547 10.1016/S0040-4039(00)74547-3
38. Paquette, L. A.; Wiedeman, P. E.; Bulman-Page, P. C. J. Org. Chem. 1988, 53, 1441 10.1021/jo00242a019
39. Paquette, L. A.; Bulman-Page, P. C.; Pansegrau, P. D.; Wiedeman, P. E. J. Org. Chem. 1988, 53, 1450 10.1021/jo00242a020
40. Paquette, L. A.; Pansegrau, P. D.; Wiedeman, P. E.; Springer, J. P. J. Org. Chem. 1988, 53, 1461 10.1021/jo00242a021
41. Bacque, E.; Pautrat, F.; Zard, S. Z. Org. Lett. 2003, 5, 325 10.1021/ol027312m
42. Findley, T. J. K.; Sucunza, D.; Miller, L. C.; Helm, M. D.; Helliwell, M.; Davies, D. T.; Procter, D. J. Org. Biomol. Chem. 2011, 9, 2433 10.1039/c0ob01086c
43. Lotesta, S. D.; Liu, J.; Yates, E. V.; Krieger, I.; Sacchettini, J. C.; Freundlich, J. S.; Sorensen, E. J. Chem. Sci. 2011, 2, 1258 10.1039/c1sc00116g
44. Liu, J.; Lotesta, S. D.; Sorensen, E. J. Chem. Commun. 2011, 47, 1500 10.1039/C0CC04077K
45. For a discussion of step-economy, see: Wender, P. A.; Verma, V. A.; Paxton, T. J.; Pillow, T. H. Acc. Chem. Res. 2008, 41, 40 10.1021/ar700155p
46. Takai, K.; Kimura, K.; Kuroda, T.; Hiyama, T.; Nozaki, H. Tetrahedron Lett. 1983, 24, 5281 10.1016/S0040-4039(00)88417-8
47. Jin, H.; Uenishi, J.; Christ, W. J.; Kishi, Y. J. Am. Chem. Soc. 1986, 108, 5644 10.1021/ja00278a057
48. Takai, K. Addition of Organochromium Reagents to Carbonyl Compounds. In Organic Reactions; John Wiley & Sons, Inc.: Hoboken, 2004; pp 253-612.
49. For an early example, see: Kablaoui, N. M.; Buchwald, S. L. J. Am. Chem. Soc. 1995, 117, 6785 10.1021/ja00130a021
50. Moslin, R. M.; Miller-Moslin, K.; Jamison, T. F. Chem. Commun. 2007, 4441 10.1039/b707737h
51. Jackson, E. P.; Malik, H. A.; Sormunen, G. J.; Baxter, R. D.; Liu, P.; Wang, H.; Shareef, A.-R.; Montgomery, J. Acc. Chem. Res. 2015, 48, 1736 10.1021/acs.accounts.5b00096
52. Carey, F. A.; Sundberg, R. J. 3.4 Carbocyclic Rings Other Than Six-Membered. In Advanced Organic Chemistry; 3 rd ed.; Plenum: New York, 1990; Vol. A, pp 141-144.
53. Illuminati, G.; Mandolini, L.; Masci, B. J. Am. Chem. Soc. 1975, 97, 4960 10.1021/ja00850a032
54. Morita, Y.; Suzuki, M.; Noyori, R. J. Org. Chem. 1989, 54, 1785 10.1021/jo00269a006
55. Mander, L. N.; Sethi, S. P. Tetrahedron Lett. 1983, 24, 5425 10.1016/S0040-4039(00)87886-7
56. Heller, S. T.; Sarpong, R. Org. Lett. 2010, 12, 4572 10.1021/ol1018882
57. Crisp, G. T.; Scott, W. J.; Stille, J. K. J. Am. Chem. Soc. 1984, 106, 7500 10.1021/ja00336a033
58. He, W.; Sun, X.; Frontier, A. J. J. Am. Chem. Soc. 2003, 125, 14278 10.1021/ja037910b
59. MacAlpine, G. A.; Raphael, R. A.; Shaw, A.; Taylor, A. W.; Wild, H.-J. J. Chem. Soc., Chem. Commun. 1974, 834 10.1039/C39740000834
60. Karpf, M.; Dreiding, A. S. Helv. Chim. Acta 1976, 59, 1226 10.1002/hlca.19760590425
61. Hiyama, T.; Shinoda, M.; Saimoto, H.; Nozaki, H. Bull. Chem. Soc. Jpn. 1981, 54, 2747 10.1246/bcsj.54.2747
62. Hosokawa, S.; Sekiguchi, K.; Enemoto, M.; Kobayashi, S. Tetrahedron Lett. 2000, 41, 6429 10.1016/S0040-4039(00)00937-0
63. Zhang, Y.; Rovis, T. J. Am. Chem. Soc. 2004, 126, 15964 10.1021/ja044113k
64. Wotal, A. C.; Weix, D. J. Org. Lett. 2012, 14, 1476 10.1021/ol300217x
65. Weix, D. J. Acc. Chem. Res. 2015, 48, 1767 10.1021/acs.accounts.5b00057
66. Katritzky, A. R.; Yao, J.; Qi, M. J. Org. Chem. 1997, 62, 8201 10.1021/jo971234c
67. Cacchi, S.; Morera, E.; Ortar, G. Synthesis 1986, 1986, 320 10.1055/s-1986-31599
68. Genin, E.; Toullec, P. Y.; Antoniotti, S.; Brancour, C.; Genêt, J.-P.; Michelet, V. J. Am. Chem. Soc. 2006, 128, 3112 10.1021/ja056857j
69. Dorel, R.; Echavarren, A. M. Chem. Rev. 2015, 115, 9028 10.1021/cr500691k
70. Trost, B. M.; Jiang, C. J. Am. Chem. Soc. 2001, 123, 12907 10.1021/ja012104v
71. Williams, J. M.; Jobson, R. B.; Yasuda, N.; Marchesini, G.; Dolling, U.-H.; Grabowski, E. J. J. Tetrahedron Lett. 1995, 36, 5461 10.1016/0040-4039(95)01089-Z
72. Feringa, B. L.; Pineschi, M.; Arnold, L. A.; Imbos, R.; de Vries, A. H. M. Angew. Chem., Int. Ed. Engl. 1997, 36, 2620 10.1002/anie.199726201
73. Tanino, K.; Onuki, K.; Asano, K.; Miyashita, M.; Nakamura, T.; Takahashi, Y.; Kuwajima, I. J. Am. Chem. Soc. 2003, 125, 1498 10.1021/ja029226n
74. Comins, D. L.; Dehghani, A. Tetrahedron Lett. 1992, 33, 6299 10.1016/S0040-4039(00)60957-7
75. Gagnier, S. V.; Larock, R. C. J. Am. Chem. Soc. 2003, 125, 4804 10.1021/ja0212009
76. Larionov, O. V.; Corey, E. J. Org. Lett. 2010, 12, 300 10.1021/ol902643w
77. Boeckman, R. K.; Bruza, K. J. J. Org. Chem. 1979, 44, 4781 10.1021/jo00394a008
78. Kramer, R.; Brückner, R. Eur. J. Org. Chem. 2013, 2013, 6563 10.1002/ejoc.201300182
79. Yoshikai, N.; Nakamura, E. Chem. Rev. 2012, 112, 2339 10.1021/cr200241f
80. Lipshutz, B. H.; Elsworth, E. L.; Siahaan, T. J. J. Am. Chem. Soc. 1989, 111, 1351 10.1021/ja00186a031
81. For a review, see: Nagata, W.; Yoshioka, M. Hydrocyanation of Conjugated Carbonyl Compounds. In Organic Reactions; John Wiley & Sons, Inc.: New York, 2004; pp 255-476.
82. Kraus, G. A.; Frazier, K. J. Org. Chem. 1980, 45, 4262 10.1021/jo01309a052
83. Roth, G. J.; Liepold, B.; Müller, S. G.; Bestmann, H. J. Synthesis 2004, 59 10.1055/s-2003-44346
84. Shareef, A.-R.; Sherman, D. H.; Montgomery, J. Chem. Sci. 2012, 3, 892 10.1039/C2SC00866A
85. Wang, H.; Negretti, S.; Knauff, A. R.; Montgomery, J. Org. Lett. 2015, 17, 1493 10.1021/acs.orglett.5b00381
86. Dess, D. B.; Martin, J. C. J. Am. Chem. Soc. 1991, 113, 7277 10.1021/ja00019a027
87. Okutani, M.; Mori, Y. Chem. Pharm. Bull. 2015, 63, 393 10.1248/cpb.c15-00146
88. Li, L.; Zeng, M.; Herzon, S. B. Angew. Chem., Int. Ed. 2014, 53, 7892 10.1002/anie.201404320
89. Pidathala, C.; Hoang, L.; Vignola, N.; List, B. Angew. Chem., Int. Ed. 2003, 42, 2785 10.1002/anie.200351266
90. Cacchi, S.; Morera, E.; Ortar, G. Org. Synth. 2011, 88, 260 10.15227/orgsyn.088.0260
91. Gradillas, A.; Pérez-Castells, J. Angew. Chem., Int. Ed. 2006, 45, 6086 10.1002/anie.200600641
92. Hutton, T. K.; Muir, K.; Procter, D. J. Org. Lett. 2002, 4, 2345 10.1021/ol0260472