Macrocyclic drugs and synthetic methodologies toward macrocycles

Molecules

Volumn 18, Issue 6, 2013, Pages 6230-6268

  Yu, Xufen ^a   Sun, Dianqing ^a  

^a UNIVERSITY OF HAWAII AT HILO   (United States)

Author keywords

Macrocycles; Macrocyclic drugs; Macrocyclization; Macrolactamization; Macrolactonization; Methodology; Natural products; Retrosynthesis; Transition metal catalyzed cross coupling; ring closing metathesis; click chemistry

Indexed keywords

DRUG; MACROCYCLIC COMPOUND;

CHEMISTRY; CYCLIZATION; METHODOLOGY; REVIEW; SYNTHESIS; PROCEDURES;

CHEMISTRY TECHNIQUES, SYNTHETIC; CYCLIZATION; MACROCYCLIC COMPOUNDS; PHARMACEUTICAL PREPARATIONS;

EID: 84879641206     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules18066230     Document Type: Review

References (237)

1. Driggers, E.M.; Hale, S.P.; Lee, J.; Terrett, N.K. The exploration of macrocycles for drug discovery-An underexploited structural class. Nat. Rev. Drug Discov. 2008, 7, 608-624.
2. Mallinson, J.; Collins, I., Macrocycles in new drug discovery. Fut. Med. Chem. 2012, 4, 1409-1438.
3. Krahn, D.; Ottmann, C.; Kaiser, M. Macrocyclic proteasome inhibitors. Curr. Med. Chem. 2011, 18, 5052-5060.
4. Marsault, E.; Peterson, M.L. Macrocycles Are Great Cycles: Applications, Opportunities, and Challenges of Synthetic Macrocycles in Drug Discovery. J. Med. Chem. 2011, 54, 1961-2004.
5. Erb, W.; Zhu, J. From natural product to marketed drug: The tiacumicin odyssey. Nat. Prod. Rep. 2013, 30, 161-174.
6. Wessjohann, L.A.; Ruijter, E.; Garcia-Rivera, D.; Brandt, W. What can a chemist learn from nature's macrocycles?-A brief, conceptual view. Mol. Divers. 2005, 9, 171-186.
7. Ruan, B.F.; Zhu, H.L. The chemistry and biology of the bryostatins: Potential PKC inhibitors in clinical development. Curr. Med. Chem. 2012, 19, 2652-2664.
8. Lipinski, C.A.; Lombardo, F.; Dominy, B.W.; Feeney, P.J. Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv. Drug Deliv. Rev. 2001, 46, 3-26.
9. Rybak, M.; Lomaestro, B.; Rotschafer, J.C.; Moellering, R.; Craig, W.; Billeter, M.; Dalovisio, J.R.; Levine, D.P. Therapeutic monitoring of vancomycin in adult patients: A consensus review of the American Society of Health-System Pharmacists, the Infectious Diseases Society of America, and the Society of Infectious Diseases Pharmacists. Am. J. Health Syst. Pharm. 2009, 66, 82-98.
10. Lexi-Comp OnlineTM. Medical database. Lexi-Comp, Inc.: Hudson, OH, USA, 2013.
11. Dunbar, L.M.; Tang, D.M.; Manausa, R.M. A review of telavancin in the treatment of complicated skin and skin structure infections (cSSSI). Ther. Clin. Risk Manag. 2008, 4, 235-244.
12. Saravolatz, L.D.; Stein, G.E.; Johnson, L.B. Telavancin: A Novel Lipoglycopeptide. Clin. Infect. Dis. 2009, 49, 1908-1914.
13. Higgins, D.L.; Chang, R.; Debabov, D.V.; Leung, J.; Wu, T.; Krause, K.M.; Sandvik, E.; Hubbard, J.M.; Kaniga, K.; Schmidt, D.E.; et al. Telavancin, a Multifunctional Lipoglycopeptide, Disrupts both Cell Wall Synthesis and Cell Membrane Integrity in Methicillin-Resistant Staphylococcus aureus. Antimicrob. Agents Chemother. 2005, 49, 1127-1134.
14. Lunde, C.S.; Hartouni, S.R.; Janc, J.W.; Mammen, M.; Humphrey, P.P.; Benton, B.M. Telavancin Disrupts the Functional Integrity of the Bacterial Membrane through Targeted Interaction with the Cell Wall Precursor Lipid II. Antimicrob. Agents Chemother. 2009, 53, 3375-3383.
15. Jones, R.N.; Barry, A.L. Antimicrobial activity and spectrum of LY146032, a lipopeptide antibiotic, including susceptibility testing recommendations. Antimicrob. Agents Chemother. 1987, 31, 625-629.
16. Steenbergen, J.N.; Alder, J.; Thorne, G.M.; Tally, F.P. Daptomycin: A lipopeptide antibiotic for the treatment of serious Gram-positive infections. J. Antimicrob. Chemother. 2005, 55, 283-288.
17. Hurdle, J.G.; O'Neill, A.J.; Chopra, I.; Lee, R.E. Targeting bacterial membrane function: An underexploited mechanism for treating persistent infections. Nat. Rev. Microbiol. 2011, 9, 62-75.
18. Whitman, C.B.; Czosnowski, Q.A. Fidaxomicin for the treatment of Clostridium difficile infections. Ann. Pharmacother. 2012, 46, 219-228.
19. Hardesty, J.S.; Juang, P. Fidaxomicin: A macrocyclic antibiotic for the treatment of Clostridium difficile infection. Pharmacotherapy 2011, 31, 877-886.
20. Gerber, M.; Ackermann, G. OPT-80, a macrocyclic antimicrobial agent for the treatment of Clostridium difficile infections: A review. Expert Opin. Investig. Drugs 2008, 17, 547-553.
21. Johnson, B.A.; Anker, H.; Meleney, F.L. Bacitracin: A new antibiotic produced by a member of the B. subtilis group. Science 1945, 102, 376-377.
22. Ohki, R.; Tateno, K.; Okada, Y.; Okajima, H.; Asai, K.; Sadaie, Y.; Murata, M.; Aiso, T. A Bacitracin-Resistant Bacillus subtilis Gene Encodes a Homologue of the Membrane-Spanning Subunit of the Bacillus licheniformis ABC Transporter. J. Bacteriol. 2003, 185, 51-59.
23. Stone, K.J.; Strominger, J.L. Mechanism of Action of Bacitracin: Complexation with Metal Ion and C55-Isoprenyl Pyrophosphate. Proc. Natl. Acad. Sci. USA 1971, 68, 3223-3227.
24. Falagas, M.E.; Kasiakou, S.K.; Saravolatz, L.D. Colistin: The Revival of Polymyxins for the Management of Multidrug-Resistant Gram-Negative Bacterial Infections. Clin. Infect. Dis. 2005, 40, 1333-1341.
25. Michalopoulos, A.; Falagas, M.E. Colistin and Polymyxin B in Critical Care. Crit. Care Clin. 2008, 24, 377-391.
26. Evans, M.E.; Feola, D.J.; Rapp, R.P. Polymyxin B sulfate and colistin: Old antibiotics for emerging multiresistant gram-negative bacteria. Ann. Pharmacother. 1999, 33, 960-967.
27. McDaniel, R.; Welch, M.; Hutchinson, C.R. Genetic Approaches to Polyketide Antibiotics. 1. Chem. Rev. 2005, 105, 543-558.
28. Ma, X.; Ma, S. Significant breakthroughs in search for anti-infectious agents derived from erythromycin A. Curr. Med. Chem. 2011, 18, 1993-2015.
29. Alvarez-Elcoro, S.; Enzler, M.J. The Macrolides: Erythromycin, Clarithromycin, and Azithromycin. Mayo Clin. Proc. 1999, 74, 613-634.
30. Zuckerman, J.M.; Qamar, F.; Bono, B.R. Review of Macrolides (Azithromycin, Clarithromycin), Ketolids (Telithromycin) and Glycylcyclines (Tigecycline). Med. Clin. N. Am. 2011, 95, 761-791.
31. Ackermann, G.; Rodloff, A.C. Drugs of the 21st century: Telithromycin (HMR 3647)-the first ketolide. J. Antimicrob. Chemother. 2003, 51, 497-511.
32. Zhanel, G.; Dueck, M.; Hoban, D.; Vercaigne, L.; Embil, J.; Gin, A.; Karlowsky, J. Review of Macrolides and Ketolides. Drugs 2001, 61, 443-498.
33. Rubinstein, E.; Keller, N. Spiramycin renaissance. J. Antimicrob. Chemother. 1998, 42, 572-576.
34. Mukhtar, T.A.; Wright, G.D. Streptogramins, Oxazolidinones, and Other Inhibitors of Bacterial Protein Synthesis. Chem. Rev. 2005, 105, 529-542.
35. Allington, D.R.; Rivey, M.P. Quinupristin/dalfopristin: A therapeutic review. Clin. Ther. 2001, 23, 24-44.
36. Chopra, I. Bacterial RNA polymerase: A promising target for the discovery of new antimicrobial agents. Curr. Opin. Investig. Drugs 2007, 8, 600-607.
37. Johansen, S.K.; Maus, C.E.; Plikaytis, B.B.; Douthwaite, S. Capreomycin Binds across the Ribosomal Subunit Interface Using tlyA-Encoded 22-O-Methylations in 16S and 23S rRNAs. Mol. Cell 2006, 23, 173-182.
38. Kathiravan, M.K.; Salake, A.B.; Chothe, A.S.; Dudhe, P.B.; Watode, R.P.; Mukta, M.S.; Gadhwe, S. The biology and chemistry of antifungal agents: A review. Bioorg. Med. Chem. 2012, 20, 5678-5698.
39. Odds, F.C.; Brown, A.J.P.; Gow, N.A.R. Antifungal agents: Mechanisms of action. Trends Microbiol. 2003, 11, 272-279.
40. Chen, S.C.A.; Slavin, M.A.; Sorrell, T.C. Echinocandin antifungal drugs in fungal infections: A comparison. Drugs 2011, 71, 11-41.
41. Holt, S.L.; Drew, R.H. Echinocandins: Addressing outstanding questions surrounding treatment of invasive fungal infections. Am. J. Health Syst. Pharm. 2011, 68, 1207-1220.
42. Wiederhold, N.P.; Lewis, R.E. The echinocandin antifungals: An overview of the pharmacology, spectrum and clinical efficacy. Expert Opin. Investig. Drugs 2003, 12, 1313-1333.
43. Campbell, W.C.; Fisher, M.H.; Stapley, E.O.; Albers-Schönberg, G.; Jacob, T.A. Ivermectin: A potent new antiparasitic agent. Science 1983, 221, 823-828.
44. González, P.; González, F.A.; Ueno, K. Ivermectin in human medicine, an overview of the current status of its clinical applications. Curr. Pharm. Biotechnol. 2012, 13, 1103-1109.
45. Hollstein, U. Actinomycin. Chemistry and mechanism of action. Chem. Rev. 1974, 74, 625-652.
46. Bollag, D.M.; McQueney, P.A.; Zhu, J.; Hensens, O.; Koupal, L.; Liesch, J.; Goetz, M.; Lazarides, E.; Woods, C.M. Epothilones, a New Class of Microtubule-stabilizing Agents with a Taxol-like Mechanism of Action. Cancer Res. 1995, 55, 2325-2333.
47. Lee, F.Y.F.; Borzilleri, R.; Fairchild, C.R.; Kim, S.-H.; Long, B.H.; Reventos-Suarez, C.; Vite, G.D.; Rose, W.C.; Kramer, R.A. BMS-247550: A Novel Epothilone Analog with a Mode of Action Similar to Paclitaxel but Possessing Superior Antitumor Efficacy. Clin. Cancer Res. 2001, 7, 1429-1437.
48. Piekarz, R.L.; Robey, R.; Sandor, V.; Bakke, S.; Wilson, W.H.; Dahmoush, L.; Kingma, D.M.; Turner, M.L.; Altemus, R.; Bates, S.E. Inhibitor of histone deacetylation, depsipeptide (FR901228), in the treatment of peripheral and cutaneous T-cell lymphoma: A case report. Blood 2001, 98, 2865-2868.
49. Ho, S.; Clipstone, N.; Timmermann, L.; Northrop, J.; Graef, I.; Fiorentino, D.; Nourse, J.; Crabtree, G.R. The Mechanism of Action of Cyclosporin A and FK506. Clin. Immunol. Immunopathol. 1996, 80, S40-S45.
50. Groth, C.G.; Bäckman, L.; Morales, J.M.; Calne, R.; Kreis, H.; Lang, P.; Touraine, J.L.; Claesson, K.; Campistol, J.M.; Durand, D.; Wramner, L.; Brattström, C.; Charpentier, B. Sirolimus (rapamycin)-based therapy in human renal transplantation: Similar efficacy and different toxicity compared with cyclosporine. Transplantation 1999, 67, 1036-1042.
51. Graziani, E.I. Recent advances in the chemistry, biosynthesis and pharmacology of rapamycin analogs. Nat. Prod. Rep. 2009, 26, 602-609.
52. Escudier, B. Temsirolimus in the treatment of advanced renal cell carcinoma. Oncol. Rev. 2007, 1, 73-80.
53. Pawlikowski, M.; Mełeń-Mucha, G. Somatostatin analogs-From new molecules to new applications. Curr. Opin. Pharmacol. 2004, 4, 608-613.
54. Racine, M.S.; Barkan, A.L. Somatostatin analogs in medical treatment of acromegaly. Endocrine 2003, 20, 271-278.
55. Feelders, R.A.; Hofland, L.J.; Van Aken, M.O.; Neggers, S.J.; Lamberts, S.W.J.; de Herder, W.W.; van der Lely, A.J. Medical therapy of acromegaly: Efficacy and safety of somatostatin analogues. Drugs 2009, 69, 2207-2226.
56. Collins, J.C.; James, K., Emac-A comparative index for the assessment of macrocyclization efficiency. Med. Chem. Commun. 2012, 3, 1489-1495.
57. Harrowven, D.C.; Kostiuk, S.L. Macrocylic bisbibenzyl natural products and their chemical synthesis. Nat. Prod. Rep. 2012, 29, 223-242.
58. Terrett, N.K. Methods for the synthesis of macrocycle libraries for drug discovery. Drug Discov. Today Technol. 2010, 7, e97-e104.
59. Wessjohann, L.; Ruijter, E. Strategies for Total and Diversity-Oriented Synthesis of Natural Product(-Like) Macrocycles. In Natural Product Synthesis I; Springer Berlin Heidelberg: Berlin, Germany, 2005; Volume 243, pp. 137-184.
60. Horton, A.E.; May, O.S.; Elsegood, M.R.J.; Kimber, M.C. Total synthesis of the marine-derived cyclic depsipeptide alternaramide. Synlett 2011, 22, 797-800.
61. Parenty, A.; Moreau, X.; Niel, G.; Campagne, J.M. Update 1 of: Macrolactonizations in the Total Synthesis of Natural Products. Chem. Rev. 2013, 113, PR1-PR40.
62. Corey, E.J.; Nicolaou, K.C. Efficient and mild lactonization method for the synthesis of macrolides. J. Am. Chem. Soc. 1974, 96, 5614-5616.
63. Palomo, C.; Oiarbide, M.; García, J.M.; González, A.; Pazos, R.; Odriozola, J.M.; Bañuelos, P.; Tello, M.; Linden, A. A Practical Total Synthesis of Hapalosin, a 12-Membered Cyclic Depsipeptide with Multidrug Resistance-Reversing Activity, by Employing Improved Segment Coupling and Macrolactonization. J. Org. Chem. 2004, 69, 4126-4134.
64. Corey, E.J.; Clark, D.A. A new method for the synthesis of 2-pyridinethiol carboxylic esters. Tetrahedron Lett. 1979, 20, 2875-2878.
65. Corey, E.J.; Brunelle, D.J. New reagents for the conversion of hydroxy acids to macrolactones by the double activation method. Tetrahedron Lett. 1976, 17, 3409-3412.
66. Schnorrenberg, G.; Steglich, W. Economic Synthesis of Activated N-tert-Butyloxycarbonyl Amino Acid Esters. Angew. Chem. Int. Ed. Engl. 1979, 18, 307-308.
67. Nimitz, J.S.; Wollenberg, R.H. Macrolide ring closure. Silver ion promoted lactonization of ω-hydroxy thiolesters of 2-amino-4-mercapto-6- methylpyrimidine. Tetrahedron Lett. 1978, 19, 3523-3526.
68. Mukaiyama, T.; Usui, M.; Saigo, K. The facile synthesis of lactones. Chem. Lett. 1976, 5, 49-50.
69. Venkataraman, K.; Wagle, D.R. Cyanuric chloride, a useful reagent for macrocyclic lactonization. Tetrahedron Lett. 1980, 21, 1893-1896.
70. Inanaga, J.; Hirata, K.; Saeki, H.; Katsuki, T.; Yamaguchi, M. A Rapid Esterification by Means of Mixed Anhydride and Its Application to Large-ring Lactonization. Bull. Chem. Soc. Jpn. 1979, 52, 1989-1993.
71. Hikota, M.; Tone, H.; Horita, K.; Yonemitsu, O. Chiral synthesis of polyketide-derived natural products. 27. Stereoselective synthesis of erythronolide A via an extremely efficient macrolactonization by the modified Yamaguchi method. J. Org. Chem. 1990, 55, 7-9.
72. Tatsuta, K. Total synthesis of the big four antibiotics and related antibiotics. J. Antibiot. 2013, 66, 107-129.
73. Xie, L.; Zhu, S.-Y.; Shen, X.-Q.; He, L.-L.; Yang, J.-S. Total Synthesis of Batatoside L. J. Org. Chem. 2010, 75, 5764-5767.
74. Yin, Y.; Li, Y.; Kong, L. Pentasaccharide Glycosides from the Tubers of Sweet Potato (Ipomoea batatas). J. Agric. Food Chem. 2008, 56, 2363-2368.
75. Yin, Y.-Q.; Wang, J.-S.; Luo, J.-G.; Kong, L.-Y. Novel acylated lipo-oligosaccharides from the tubers of Ipomoea batatas. Carbohydr. Res. 2009, 344, 466-473.
76. García-Fortanet, J.; Murga, J.; Carda, M.; Marco, J.A.; Matesanz, R.; Díaz, J.F.; Barasoain, I. The total synthesis and biological properties of the cytotoxic macrolide FD-891 and its non-natural (Z)-C12 isomer. Chem. Eur. J. 2007, 13, 5060-5074.
77. García-Fortanet, J.; Murga, J.; Carda, M.; Marco, J.A. Stereoselective synthesis of the cytotoxic macrolide FD-891. Org. Lett. 2006, 8, 2695-2698.
78. Crimmins, M.T.; Caussanel, F. Enantioselective total synthesis of FD-891. J. Am. Chem. Soc. 2006, 128, 3128-3129.
79. Seki-Asano, M.; Tsuchida, Y.; Hanada, K.; Mizoue, K. Structures of new 18-membered macrolides FD-891 and FD-892. J. Antibiot. 1994, 47, 1234-1241.
80. Eguchi, T.; Yamamoto, K.; Mizoue, K.; Kakinuma, K. Structure revision of FD-891, a 16-membered macrolide antibiotic. J. Antibiot. 2004, 57, 156-157.
81. Yadav, J.S.; Das, S.K.; Sabitha, G. Stereoselective Total Synthesis of FD-891. J. Org. Chem. 2012, 77, 11109-11118.
82. Woodward, R.B.; Bader, F.E.; Bickel, H.; Frey, A.J.; Kierstead, R.W. The total synthesis of reserpine. Tetrahedron 1958, 2, 1-57.
83. Boden, E.P.; Keck, G.E. Proton-transfer steps in Steglich esterification: A very practical new method for macrolactonization. J. Org. Chem. 1985, 50, 2394-2395.
84. Lee, E.; Jeong, E.J.; Kang, E.J.; Sung, L.T.; Hong, S.K. Total Synthesis of Pamamycin-607. J. Am. Chem. Soc. 2001, 123, 10131-10132.
85. Swamy, K.C.K.; Kumar, N.N.B.; Balaraman, E.; Kumar, K.V.P.P. Mitsunobu and Related Reactions: Advances and Applications. Chem. Rev. 2009, 109, 2551-2651.
86. Ehrlich, G.; Hassfeld, J.; Eggert, U.; Kalesse, M. The Total Synthesis of (+)-Tedanolide. J. Am. Chem. Soc. 2006, 128, 14038-14039.
87. Xu, Y.; Chen, L.; Duan, X.; Meng, Y.; Jiang, L.; Li, M.; Zhao, G.; Li, Y. Total synthesis of hirsutellide A. Tetrahedron Lett. 2005, 46, 4377-4379.
88. Kunishima, M.; Kawachi, C.; Hioki, K.; Terao, K.; Tani, S. Formation of carboxamides by direct condensation of carboxylic acids and amines in alcohols using a new alcohol- and water-soluble condensing agent: DMT-MM. Tetrahedron 2001, 57, 1551-1558.
89. McCauley, J.A.; McIntyre, C.J.; Rudd, M.T.; Nguyen, K.T.; Romano, J.J.; Butcher, J.W.; Gilbert, K.F.; Bush, K.J.; Holloway, M.K.; Swestock, J.; et al. Discovery of Vaniprevir (MK-7009), a Macrocyclic Hepatitis C Virus NS3/4a Protease Inhibitor. J. Med. Chem. 2010, 53, 2443-2463.
90. Song, Z.J.; Tellers, D.M.; Journet, M.; Kuethe, J.T.; Lieberman, D.; Humphrey, G.; Zhang, F.; Peng, Z.; Waters, M.S.; Zewge, D.; et al. Synthesis of Vaniprevir (MK-7009): Lactamization To Prepare a 22-Membered Macrocycle. J. Org. Chem. 2011, 76, 7804-7815.
91. Zhang, W.; Moore, J.S. Shape-persistent macrocycles: Structures and synthetic approaches from arylene and ethynylene building blocks. Angew. Chem. Int. Ed. 2006, 45, 4416-4439.
92. Sasse, F.; Steinmetz, H.; Hofle, G.; Reichenbach, H. Rhizopodin, a new compound from Myxococcus stipitatus (myxobacteria) causes formation of rhizopodia-like structures in animal cell cultures: Production, isolation, physico-chemical and biological properties. J. Antibiot. 1993, 46, 741-748.
93. Jansen, R.; Steinmetz, H.; Sasse, F.; Schubert, W.-D.; Hagelüken, G.; Albrecht, S.C.; Müller, R. Isolation and structure revision of the actin-binding macrolide rhizopodin from Myxococcus stipitatus (Myxobacteria). Tetrahedron Lett. 2008, 49, 5796-5799.
94. Dieckmann, M.; Rudolph, S.; Dreisigacker, S.; Menche, D. Concise synthesis of the macrocyclic core of rhizopodin by a heck macrocyclization strategy. J. Org. Chem. 2012, 77, 10782-10788.
95. Dieckmann, M.; Kretschmer, M.; Li, P.; Rudolph, S.; Herkommer, D.; Menche, D. Total synthesis of rhizopodin. Angew. Chem. Int. Ed. 2012, 51, 5667-5670.
96. Pulukuri, K.K.; Chakraborty, T.K. Stereoselective synthesis of the monomeric unit of actin binding macrolide rhizopodin. Org. Lett. 2012, 14, 2858-2861.
97. Kretschmer, M.; Menche, D. Stereocontrolled synthesis of the C8-C22 fragment of rhizopodin. Org. Lett. 2012, 14, 382-385.
98. Chakraborty, T.K.; Sreekanth, M.; Pulukuri, K.K. Synthetic studies toward potent cytostatic macrolide rhizopodin: Stereoselective synthesis of the C16-C28 fragment. Tetrahedron Lett. 2011, 52, 59-61.
99. Chakraborty, T.K.; Pulukuri, K.K.; Sreekanth, M. Studies directed toward the synthesis of rhizopodin: Stereoselective synthesis of the C1-C15 fragment. Tetrahedron Lett. 2010, 51, 6444-6446.
100. Chen, Z.; Song, L.; Xu, Z.; Ye, T. Synthesis of the C9-C23 (C9'-C23') fragment of the dimeric natural product rhizopodin. Org. Lett. 2010, 12, 2036-2039.
101. Hagelueken, G.; Albrecht, S.C.; Steinmetz, H.; Jansen, R.; Heinz, D.W.; Kalesse, M.; Schubert, W.D. The absolute configuration of rhizopodin and its inhibition of actin polymerization by dimerization. Angew. Chem. Int. Ed. 2009, 48, 595-598.
102. Velvadapu, V.; Paul, T.; Wagh, B.; Glassford, I.; DeBrosse, C.; Andrade, R.B. Total Synthesis of (-)-4,8,10-Tridesmethyl Telithromycin. J. Org. Chem. 2011, 76, 7516-7527.
103. Ezaki, M.; Iwami, M.; Yamashita, M.; Hashimoto, S.; Komori, T.; Umehara, K.; Mine, Y.; Kohsaka, M.; Aoki, H.; Imanaka, H. Biphenomycins A and B, novel peptide antibiotics. I. Taxonomy, fermentation, isolation and characterization. J. Antibiot. 1985, 38, 1453-1461.
104. Uchida, I.; Ezaki, M.; Shigematsu, N.; Hashimoto, M. Structure of WS-43708A, a novel cyclic peptide antibiotic. J. Org. Chem. 1985, 50, 1341-1342.
105. Lépine, R.; Zhu, J. Microwave-Assisted Intramolecular Suzuki-Miyaura Reaction to Macrocycle, a Concise Asymmetric Total Synthesis of Biphenomycin B. Org. Lett. 2005, 7, 2981-2984.
106. Unsworth, W.P.; Gallagher, K.A.; Jean, M.; Schmidt, J.P.; Diorazio, L.J.; Taylor, R.J.K. Direct Imine Acylation: Synthesis of the Proposed Structures of 'Upenamide. Org. Lett. 2013, 15, 262-265.
107. Abe, H.; Chida, Y.; Kurokawa, H.; Inouye, M. Selective Binding of D2h-Symmetrical, Acetylene-Linked Pyridine/Pyridone Macrocycles to Maltoside. J. Org. Chem. 2011, 76, 3366-3371.
108. Yamasaki, R.; Shigeto, A.; Saito, S. Preparation of Shape-Persistent Macrocycles with a Single Pyridine Unit by Double Cross-Coupling Reactions of Aryl Bromides and Alkynes. J. Org. Chem. 2011, 76, 10299-10305.
109. Hassan, J.; Sévignon, M.; Gozzi, C.; Schulz, E.; Lemaire, M. Aryl-Aryl Bond Formation One Century after the Discovery of the Ullmann Reaction. Chem. Rev. 2002, 102, 1359-1470.
110. Isaka, M.; Rugseree, N.; Maithip, P.; Kongsaeree, P.; Prabpai, S.; Thebtaranonth, Y. Hirsutellones A-E, antimycobacterial alkaloids from the insect pathogenic fungus Hirsutella nivea BCC 2594. Tetrahedron 2005, 61, 5577-5583.
111. Halvorsen, G.T.; Roush, W.R. Stereoselective synthesis of the decahydrofluorene core of the hirsutellones. Tetrahedron Lett. 2011, 52, 2072-2075.
112. Huang, M.; Huang, C.; Liu, B. Studies toward the total synthesis of the hirsutellones. Tetrahedron Lett. 2009, 50, 2797-2800.
113. Huang, M.; Song, L.; Liu, B. Construction of the Cyclophane Core of the Hirsutellones via a RCM Strategy. Org. Lett. 2010, 12, 2504-2507.
114. Nicolaou, K.C.; Sarlah, D.; Wu, T.R.; Zhan, W. Total Synthesis of Hirsutellone B. Angew. Chem. Int. Ed. 2009, 48, 6870-6874.
115. Nicolaou, K.C.; Sun, Y.-P.; Sarlah, D.; Zhan, W.; Wu, T.R. Bioinspired Synthesis of Hirsutellones A, B, and C. Org. Lett. 2011, 13, 5708-5710.
116. Tilley, S.D.; Reber, K.P.; Sorensen, E.J. A Rapid, Asymmetric Synthesis of the Decahydrofluorene Core of the Hirsutellones. Org. Lett. 2009, 11, 701-703.
117. Uchiro, H.; Kato, R.; Arai, Y.; Hasegawa, M.; Kobayakawa, Y. Total Synthesis of Hirsutellone B via Ullmann-Type Direct 13-Membered Macrocyclization. Org. Lett. 2011, 13, 6268-6271.
118. Sharma, A.; Appukkuttan, P.; van der Eycken, E. Microwave-assisted synthesis of medium-sized heterocycles. Chem. Commun. 2012, 48, 1623-1637.
119. Su, Q.; Beeler, A.B.; Lobkovsky, E.; Porco, J.A.; Panek, J.S. Stereochemical Diversity through Cyclodimerization: Synthesis of Polyketide-like Macrodiolides. Org. Lett. 2003, 5, 2149-2152.
120. Pérez-Balado, C.; Nebbioso, A.; Rodríguez-Graña, P.; Minichiello, A.; Miceli, M.; Altucci, L.; de Lera, Á.R. Bispyridinium Dienes: Histone Deacetylase Inhibitors with Selective Activities. J. Med. Chem. 2007, 50, 2497-2505.
121. Afonso, A.; Feliu, L.; Planas, M. Solid-phase synthesis of biaryl cyclic peptides by borylation and microwave-assisted intramolecular Suzuki-Miyaura reaction. Tetrahedron 2011, 67, 2238-2245.
122. Nnanabu, E.; Burgess, K. Cyclic Semipeptoids: Peptoid-Organic Hybrid Macrocycles. Org. Lett. 2006, 8, 1259-1262.
123. Bedard, A.-C.; Collins, S.K. Microwave accelerated Glaser-Hay macrocyclizations at high concentrations. Chem. Commun. 2012, 48, 6420-6422.
124. Dong, H.; Limberakis, C.; Liras, S.; Price, D.; James, K. Peptidic macrocyclization via palladium-catalyzed chemoselective indole C-2 arylation. Chem. Commun. 2012, 48, 11644-11646.
125. Shen, L.; Simmons, C.J.; Sun, D. Microwave-assisted synthesis of macrocycles via intramolecular and/or bimolecular Ullmann coupling. Tetrahedron Lett. 2012, 53, 4173-4178.
126. Shen, L.; Sun, D. Total synthesis and structural revision of engelhardione. Tetrahedron Lett. 2011, 52, 4570-4574.
127. Shen;, L.; Maddox, M.M.; Adhikari, S.; Bruhn, D.F.; Kumar, M.; Lee, R.E.; Hurdle, J.G.; Lee, R.E.; Sun, D. Syntheses and evaluation of macrocyclic engelhardione analogs as antitubercular and antibacterial agents. J. Antibiot. 2013, in press, doi:10.1038/ja.2013.21.
128. Lundgren, R.J.; Stradiotto, M. Recent advances in the buchwald-hartwig amination reaction enabled by the application of sterically demanding phosphine ancillary ligands. Aldrichimica Acta 2012, 45, 59-62.
129. Tsuchiya, K. Synthesis of macrocyclic aromatic amines via C-N coupling reaction. Yuki Gosei Kagaku Kyokaishi 2011, 69, 169-170.
130. Huang, K.H.; Veal, J.M.; Fadden, R.P.; Rice, J.W.; Eaves, J.; Strachan, J.-P.; Barabasz, A.F.; Foley, B.E.; Barta, T.E.; Ma, W.; et al. Discovery of Novel 2-Aminobenzamide Inhibitors of Heat Shock Protein 90 as Potent, Selective and Orally Active Antitumor Agents. J. Med. Chem. 2009, 52, 4288-4305.
131. Zapf, C.W.; Bloom, J.D.; McBean, J.L.; Dushin, R.G.; Nittoli, T.; Ingalls, C.; Sutherland, A.G.; Sonye, J.P.; Eid, C.N.; Golas, J.; et al. Design and SAR of macrocyclic Hsp90 inhibitors with increased metabolic stability and potent cell-proliferation activity. Bioorg. Med. Chem. Lett. 2011, 21, 2278-2282.
132. Zapf, C.W.; Bloom, J.D.; McBean, J.L.; Dushin, R.G.; Nittoli, T.; Otteng, M.; Ingalls, C.; Golas, J.M.; Liu, H.; Lucas, J.; et al. Macrocyclic lactams as potent Hsp90 inhibitors with excellent tumor exposure and extended biomarker activity. Bioorg. Med. Chem. Lett. 2011, 21, 3411-3416.
133. Zapf, C.W.; Bloom, J.D.; McBean, J.L.; Dushin, R.G.; Golas, J.M.; Liu, H.; Lucas, J.; Boschelli, F.; Vogan, E.; Levin, J.I. Discovery of a macrocyclic o-aminobenzamide Hsp90 inhibitor with heterocyclic tether that shows extended biomarker activity and in vivo efficacy in a mouse xenograft model. Bioorg. Med. Chem. Lett. 2011, 21, 3627-3631.
134. Grubbs, R.H.; Miller, S.J.; Fu, G.C. Ring-Closing Metathesis and Related Processes in Organic Synthesis. Acc. Chem. Res. 1995, 28, 446-452.
135. Fürstner, A. Olefin Metathesis and Beyond. Angew. Chem. Int. Ed. 2000, 39, 3012-3043.
136. Schrock, R.R.; Hoveyda, A.H. Molybdenum and Tungsten Imido Alkylidene Complexes as Efficient Olefin-Metathesis Catalysts. Angew. Chem. Int. Ed. 2003, 42, 4592-4633.
137. Connon, S. J.; Blechert, S. Recent Developments in Olefin Cross-Metathesis. Angew. Chem. Int. Ed. 2003, 42, 1900-1923.
138. Deiters, A.; Martin, S.F. Synthesis of Oxygen- and Nitrogen-Containing Heterocycles by Ring-Closing Metathesis. Chem. Rev. 2004, 104, 2199-2238.
139. Gradillas, A.; Pérez-Castells, J. Macrocyclization by Ring-Closing Metathesis in the Total Synthesis of Natural Products: Reaction Conditions and Limitations. Angew. Chem. Int. Ed. 2006, 45, 6086-6101.
140. Alcaide, B.; Almendros, P.; Luna, A. Grubbs' Ruthenium-Carbenes Beyond the Metathesis Reaction: Less Conventional Non-Metathetic Utility. Chem. Rev. 2009, 109, 3817-3858.
141. Hassan, H.M.A. Recent applications of ring-closing metathesis in the synthesis of lactams and macrolactams. Chem. Commun. 2010, 46, 9100-9106.
142. Hoveyda, A.H.; Zhugralin, A.R. The remarkable metal-catalysed olefin metathesis reaction. Nature 2007, 450, 243-251.
143. Kotha, S.; Shirbhate, M.E. Diversity-oriented approach to macrocyclic cyclophane derivatives via ring-closing metathesis. Synlett 2012, 23, 2183-2188.
144. Cutignano, A.; Bruno, I.; Bifulco, G.; Casapullo, A.; Debitus, C.; Gomez-Paloma, L.; Riccio, R. Dactylolide, a New Cytotoxic Macrolide from the Vanuatu Sponge Dactylospongia sp. Eur. J. Org. Chem. 2001, 2001, 775-778.
145. Tanaka, J.-I.; Higa, T. Zampanolide, a new cytotoxic marcrolide from a marine sponge. Tetrahedron Lett. 1996, 37, 5535-5538.
146. Field, J.J.; Singh, A.J.; Kanakkanthara, A.; Halafihi, T.I.; Northcote, P.T.; Miller, J.H. Microtubule-Stabilizing Activity of Zampanolide, a Potent Macrolide Isolated from the Tongan Marine Sponge Cacospongia mycofijiensis. J. Med. Chem. 2009, 52, 7328-7332.
147. Smith, A.B.; Safonov, I.G. Total Synthesis of (+)-Dactylolide. Org. Lett. 2002, 4, 635-637.
148. Hoye, T.R.; Hu, M. Macrolactonization via Ti(IV)-Mediated Epoxy-Acid Coupling: A Total Synthesis of (-)-Dactylolide [and Zampanolide]. J. Am. Chem. Soc. 2003, 125, 9576-9577.
149. Ding, F.; Jennings, M. P. An Expedient Total Synthesis of (-)-Dactylolide and Formal Synthesis of (-)-Zampanolide. Org. Lett. 2005, 7, 2321-2324.
150. Sanchez, C.C.; Keck, G.E. Total Synthesis of (+)-Dactylolide. Org. Lett. 2005, 7, 3053-3056.
151. Aubele, D.L.; Wan, S.; Floreancig, P.E. Total Synthesis of (+)-Dactylolide through an Efficient Sequential Peterson Olefination and Prins Cyclization Reaction. Angew. Chem. Int. Ed. 2005, 44, 3485-3488.
152. Louis, I.; Hungerford, N.L.; Humphries, E.J.; McLeod, M.D. Enantioselective Total Synthesis of (-)-Dactylolide. Org. Lett. 2006, 8, 1117-1120.
153. Uenishi, J.I.; Iwamoto, T.; Tanaka, J. Total Synthesis of (-)-Zampanolide and Questionable Existence of (-)-Dactylolide as the Elusive Biosynthetic Precursor of (-)-Zampanolide in an Okinawan Sponge. Org. Lett. 2009, 11, 3262-3265.
154. Ding, F.; Jennings, M.P. Total Synthesis of (-)-Dactylolide and Formal Synthesis of (-)-Zampanolide via Target Oriented β-C-Glycoside Formation. J. Org. Chem. 2008, 73, 5965-5976.
155. Wilson, M.R.; Taylor, R.E. Toward an Enantioselective Synthesis of (-)-Zampanolide: Preparation of the C9-C20 Region. Org. Lett. 2012, 14, 3408-3411.
156. Ghosh, A.K.; Cheng, X. Enantioselective Total Synthesis of (-)-Zampanolide, a Potent Microtubule-Stabilizing Agent. Org. Lett. 2011, 13, 4108-4111.
157. Yun, S.Y.; Hansen, E.C.; Volchkov, I.; Cho, E.J.; Lo, W.Y.; Lee, D. Total Synthesis of (-)-Dactylolide. Angew. Chem. Int. Ed. 2010, 49, 4261-4263.
158. Evano, G.; Schaus, J.V.; Panek, J.S. A Convergent Synthesis of the Macrocyclic Core of Cytotrienins: Application of RCM for Macrocyclization. Org. Lett. 2004, 6, 525-528.
159. Rossle, M.; del Valle, D.J.; Krische, M.J. Synthesis of the Cytotrienin A Core via Metal Catalyzed C-C Coupling. Org. Lett. 2011, 13, 1482-1485.
160. Hayashi, Y.; Shoji, M.; Ishikawa, H.; Yamaguchi, J.; Tamura, T.; Imai, H.; Nishigaya, Y.; Takabe, K.; Kakeya, H.; Osada, H. The Asymmetric Total Synthesis of (+)-Cytotrienin A, an Ansamycin-Type Anticancer Drug. Angew. Chem. Int. Ed. 2008, 47, 6657-6660.
161. Klapars, A.; Huang, X.; Buchwald, S.L. A General and Efficient Copper Catalyst for the Amidation of Aryl Halides. J. Am. Chem. Soc. 2002, 124, 7421-7428.
162. Lamarre, D.; Anderson, P.C.; Bailey, M.; Beaulieu, P.; Bolger, G.; Bonneau, P.; Bose, M.; Cameron, D.R.; Cartier, M.; Cordingley, M.G.; et al. An NS3 protease inhibitor with antiviral effects in humans infected with hepatitis C virus. Nature 2003, 426, 186-189.
163. Faucher, A.-M.; Bailey, M.D.; Beaulieu, P.L.; Brochu, C.; Duceppe, J.-S.; Ferland, J.-M.; Ghiro, E.; Gorys, V.; Halmos, T.; Kawai, S.H.; et al. Synthesis of BILN 2061, an HCV NS3 Protease Inhibitor with Proven Antiviral Effect in Humans. Org. Lett. 2004, 6, 2901-2904.
164. Yee, N.K.; Farina, V.; Houpis, I.N.; Haddad, N.; Frutos, R.P.; Gallou, F.; Wang, X.-J.; Wei, X.; Simpson, R.D.; Feng, X.; et al. Efficient Large-Scale Synthesis of BILN 2061, a Potent HCV Protease Inhibitor, by a Convergent Approach Based on Ring-Closing Metathesis. J. Org. Chem. 2006, 71, 7133-7145.
165. Shu, C.; Zeng, X.; Hao, M.-H.; Wei, X.; Yee, N.K.; Busacca, C.A.; Han, Z.; Farina, V.; Senanayake, C.H. RCM Macrocyclization Made Practical: An Efficient Synthesis of HCV Protease Inhibitor BILN 2061. Org. Lett. 2008, 10, 1303-1306.
166. Wei, X.; Shu, C.; Haddad, N.; Zeng, X.; Patel, N.D.; Tan, Z.; Liu, J.; Lee, H.; Shen, S.; Campbell, S.; et al. A Highly Convergent and Efficient Synthesis of a Macrocyclic Hepatitis C Virus Protease Inhibitor BI 201302. Org. Lett. 2013, 15, 1016-1019.
167. Kobayashi, J.I.; Watanabe, D.; Kawasaki, N.; Tsuda, M. Nakadomarin A, a Novel Hexacyclic Manzamine-Related Alkaloid from Amphimedon Sponge. J. Org. Chem. 1997, 62, 9236-9239.
168. Martin, D.B.C.; Vanderwal, C.D. Concise Synthesis of (-)-Nakadomarin A. Angew. Chem. Int. Ed. 2010, 49, 2830-2832.
169. Nagata, T.; Nakagawa, M.; Nishida, A. The First Total Synthesis of Nakadomarin A. J. Am. Chem. Soc. 2003, 125, 7484-7485.
170. Ono, K.; Nakagawa, M.; Nishida, A. Asymmetric Total Synthesis of (-)-Nakadomarin A. Angew. Chem. Int. Ed. 2004, 43, 2020-2023.
171. Young, I.S.; Kerr, M.A. Total Synthesis of (+)-Nakadomarin A. J. Am. Chem. Soc. 2007, 129, 1465-1469.
172. Jakubec, P.; Cockfield, D.M.; Dixon, D.J. Total Synthesis of (-)-Nakadomarin A. J. Am. Chem. Soc. 2009, 131, 16632-16633.
173. Yu, M.; Wang, C.; Kyle, A.F.; Jakubec, P.; Dixon, D.J.; Schrock, R.R.; Hoveyda, A.H. Synthesis of macrocyclic natural products by catalyst-controlled stereoselective ring-closing metathesis. Nature 2011, 479, 88-93.
174. Wang, C.; Yu, M.; Kyle, A.F.; Jakubec, P.; Dixon, D.J.; Schrock, R.R.; Hoveyda, A.H. Efficient and Selective Formation of Macrocyclic Disubstituted Z Alkenes by Ring-Closing Metathesis (RCM) Reactions Catalyzed by Mo- or W-Based Monoaryloxide Pyrrolide (MAP) Complexes: Applications to Total Syntheses of Epilachnene, Yuzu Lactone, Ambrettolide, Epothilone C, and Nakadomarin A. Chem. Eur. J. 2013, 19, 2726-2740.
175. Hoye, T.R.; Jeffrey, C.S.; Tennakoon, M.A.; Wang, J.; Zhao, H. Relay Ring-Closing Metathesis (RRCM): A Strategy for Directing Metal Movement Throughout Olefin Metathesis Sequences. J. Am. Chem. Soc. 2004, 126, 10210-10211.
176. Roethle, P.A.; Chen, I.T.; Trauner, D. Total Synthesis of (-)-Archazolid B. J. Am. Chem. Soc. 2007, 129, 8960-8961.
177. Toumi, M.; Couty, F.; Evano, G. Total Synthesis of the Cyclopeptide Alkaloid Paliurine E. Insights into Macrocyclization by Ene-Enamide RCM. J. Org. Chem. 2008, 73, 1270-1281.
178. Nicolaou, K.C.; Bulger, P.G.; Sarlah, D. Metathesis Reactions in Total Synthesis. Angew. Chem. Int. Ed. 2005, 44, 4490-4527.
179. Diver, S.T.; Giessert, A.J. Enyne Metathesis (Enyne Bond Reorganization). Chem. Rev. 2004, 104, 1317-1382.
180. Hansen, E.C.; Lee, D. Enyne Metathesis for the Formation of Macrocyclic 1,3-Dienes. J. Am. Chem. Soc. 2003, 125, 9582-9583.
181. Hansen, E.C.; Lee, D. Ring Closing Enyne Metathesis: Control over Mode Selectivity and Stereoselectivity. J. Am. Chem. Soc. 2004, 126, 15074-15080.
182. Fu, X.; Hossain, M.B.; van der Helm, D.; Schmitz, F.J. Longithorone A: Unprecedented dimeric prenylated quinone from the tunicate aplydium longithorax. J. Am. Chem. Soc. 1994, 116, 12125-12126.
183. Layton, M.E.; Morales, C.A.; Shair, M.D. Biomimetic Synthesis of (-)-Longithorone A. J. Am. Chem. Soc. 2002, 124, 773-775.
184. Collins, S.K.; El-Azizi, Y.; Schmitzer, A.R. Development of Perfluoroarene-Arene Interactions for Macrocyclic En-yne Metathesis and the Total Synthesis of Macrocyclic Natural Products. J. Org. Chem. 2007, 72, 6397-6408.
185. Fürstner, A. Alkyne Metathesis on the Rise. Angew. Chem. Int. Ed. 2013, 52, 2794-2819.
186. Wu, X.; Tamm, M. Recent advances in the development of alkyne metathesis catalysts. Beilstein J. Org. Chem. 2011, 7, 82-93.
187. Brewitz, L.; Llaveria, J.; Yada, A.; Fürstner, A. Formal Total Synthesis of the Algal Toxin (-)-Polycavernoside A. Chem. Eur. J. 2013, 19, 4532-4537.
188. Andersson, H.; Demaegdt, H.; Johnsson, A.; Vauquelin, G.; Lindeberg, G.; Hallberg, M.; Erdélyi, M.T.; Karlén, A.; Hallberg, A. Potent Macrocyclic Inhibitors of Insulin-Regulated Aminopeptidase (IRAP) by Olefin Ring-Closing Metathesis. J. Med. Chem. 2011, 54, 3779-3792.
189. Andersson, H.; Demaegdt, H.; Vauquelin, G.; Lindeberg, G.; Karlén, A.; Hallberg, M.; Erdélyi, M.T.; Hallberg, A. Disulfide Cyclized Tripeptide Analogues of Angiotensin IV as Potent and Selective Inhibitors of Insulin-Regulated Aminopeptidase (IRAP). J. Med. Chem. 2010, 53, 8059-8071.
190. Abell, A.D.; Alexander, N.A.; Aitken, S.G.; Chen, H.; Coxon, J.M.; Jones, M.A.; McNabb, S.B.; Muscroft-Taylor, A. Synthesis of Macrocyclic β-Strand Templates by Ring Closing Metathesis. J. Org. Chem. 2009, 74, 4354-4356.
191. Schreiber, S.L. Target-Oriented and Diversity-Oriented Organic Synthesis in Drug Discovery. Science 2000, 287, 1964-1969.
192. Tan, D.S. Diversity-oriented synthesis: Exploring the intersections between chemistry and biology. Nat. Chem. Biol. 2005, 1, 74-84.
193. Spring, D.R. Diversity-oriented synthesis; a challenge for synthetic chemists. Org. Biomol. Chem. 2003, 1, 3867-3870.
194. Galloway, W.R.J.D.; Spring, D.R. Is synthesis the main hurdle for the generation of diversity in compound libraries for screening? Expert Opin. Drug Discov. 2009, 4, 467-472.
195. Galloway, W.R.J.D.; Isidro-Llobet, A.; Spring, D.R. Diversity-oriented synthesis as a tool for the discovery of novel biologically active small molecules. Nat. Commun. 2010, 1, 80.
196. Kopp, F.; Stratton, C.F.; Akella, L.B.; Tan, D.S. A diversity-oriented synthesis approach to macrocycles via oxidative ring expansion. Nat. Chem. Biol. 2012, 8, 358-365.
197. Schmidt, D.R.; Kwon, O.; Schreiber, S.L. Macrolactones in diversity-oriented synthesis: Preparation of a pilot library and exploration of factors controlling macrocyclization. J. Comb. Chem. 2004, 6, 286-292.
198. Madsen, C.M.; Clausen, M.H. Biologically Active Macrocyclic Compounds-From Natural Products to Diversity-Oriented Synthesis. Eur. J. Org. Chem. 2011, 2011, 3107-3115.
199. O'Connor, C.J.; Beckmann, H.S.G.; Spring, D.R. Diversity-oriented synthesis: Producing chemical tools for dissecting biology. Chem. Soc. Rev. 2012, 41, 4444-4456.
200. Schreiber, S.L. Organic chemistry: Molecular diversity by design. Nature 2009, 457, 153-154.
201. Isidro-Llobet, A.; Murillo, T.; Bello, P.; Cilibrizzi, A.; Hodgkinson, J.T.; Galloway, W.R.J.D.; Bender, A.; Welch, M.; Spring, D.R. Diversity-oriented synthesis of macrocyclic peptidomimetics. Proc. Natl. Acad. Sci. USA 2011, 108, 6793-6798.
202. O'Connell, K.M.G.; Beckmann, H.S.G.; Laraia, L.; Horsley, H.T.; Bender, A.; Venkitaraman, A.R.; Spring, D.R. A two-directional strategy for the diversity-oriented synthesis of macrocyclic scaffolds. Org. Biomol. Chem. 2012, 10, 7545-7551.
203. Uchida, T.; Rodriquez, M.; Schreiber, S.L. Skeletally Diverse Small Molecules Using a Build/Couple/Pair Strategy. Org. Lett. 2009, 11, 1559-1562.
204. Hussain, A.; Yousuf, S.K.; Kumar, D.; Lambu, M.; Singh, B.; Maity, S.; Mukherjee, D. Intramolecular Base-Free Sonogashira Reaction for the Synthesis of Benzannulated Chiral Macrocycles Embedded in Carbohydrate Templates. Adv. Synth. Catal. 2012, 354, 1933-1940.
205. Nielsen, T.E.; Schreiber, S.L. Towards the Optimal Screening Collection: A Synthesis Strategy. Angew. Chem. Int. Ed. 2008, 47, 48-56.
206. Fitzgerald, M.E.; Mulrooney, C.A.; Duvall, J.R.; Wei, J.; Suh, B.-C.; Akella, L.B.; Vrcic, A.; Marcaurelle, L.A. Build/Couple/Pair Strategy for the Synthesis of Stereochemically Diverse Macrolactams via Head-to-Tail Cyclization. ACS Comb. Sci. 2012, 14, 89-96.
207. Dandapani, S.; Lowe, J.T.; Comer, E.; Marcaurelle, L.A. Diversity-Oriented Synthesis of 13- to 18-Membered Macrolactams via Ring-Closing Metathesis. J. Org. Chem. 2011, 76, 8042-8048.
208. Wang, Y.; Jimenez, M.; Hansen, A.S.; Raiber, E.-A.; Schreiber, S.L.; Young, D.W. Control of Olefin Geometry in Macrocyclic Ring-Closing Metathesis Using a Removable Silyl Group. J. Am. Chem. Soc. 2011, 133, 9196-9199.
209. Marx, V.M.; Herbert, M.B.; Keitz, B.K.; Grubbs, R.H. Stereoselective Access to Z and E Macrocycles by Ruthenium-Catalyzed Z-Selective Ring-Closing Metathesis and Ethenolysis. J. Am. Chem. Soc. 2012, 135, 94-97.
210. Kolb, H.C.; Finn, M.G.; Sharpless, K.B. Click Chemistry: Diverse Chemical Function from a Few Good Reactions. Angew. Chem. Int. Ed. 2001, 40, 2004-2021.
211. Umit, T. Triple click reaction strategy for macromolecular diversity. Macromol. Rapid Commun. 2013, 34, 38-46.
212. Sumerlin, B.S.; Vogt, A.P. Macromolecular Engineering through Click Chemistry and Other Efficient Transformations. Macromolecules 2009, 43, 1-13.
213. Becer, C.R.; Hoogenboom, R.; Schubert, U.S. Click Chemistry beyond Metal-Catalyzed Cycloaddition. Angew. Chem. Int. Ed. 2009, 48, 4900-4908.
214. Rostovtsev, V.V.; Green, L.G.; Fokin, V.V.; Sharpless, K.B. A Stepwise Huisgen Cycloaddition Process: Copper(I)-Catalyzed Regioselective "Ligation" of Azides and Terminal Alkynes. Angew. Chem. Int. Ed. 2002, 41, 2596-2599.
215. Tornøe, C.W.; Christensen, C.; Meldal, M. Peptidotriazoles on Solid Phase: [1,2,3]-Triazoles by Regiospecific Copper(I)-Catalyzed 1,3-Dipolar Cycloadditions of Terminal Alkynes to Azides. J. Org. Chem. 2002, 67, 3057-3064.
216. Bock, V.D.; Hiemstra, H.; van Maarseveen, J.H. CuI-Catalyzed Alkyne-Azide "Click" Cycloadditions from a Mechanistic and Synthetic Perspective. Eur. J. Org. Chem. 2006, 2006, 51-68.
217. Fournier, D.; Hoogenboom, R.; Schubert, U.S. Clicking polymers: A straightforward approach to novel macromolecular architectures. Chem. Soc. Rev. 2007, 36, 1369-1380.
218. Hawker, C.J.; Wooley, K.L. The convengence of synthetic organic and polymer chemistries. Science 2005, 309, 1200-1205.
219. Tyagi, M.; Taxak, N.; Bharatam, P.V.; Kartha, K.P.R. Synthesis of self-assembling glycerotriazolophanes. RSC Adv. 2012, 2, 11366-11371.
220. Whiting, M.; Muldoon, J.; Lin, Y.-C.; Silverman, S.M.; Lindstrom, W.; Olson, A.J.; Kolb, H.C.; Finn, M.G.; Sharpless, K.B.; Elder, J.H.; et al. Inhibitors of HIV-1 Protease by Using In Situ Click Chemistry. Angew. Chem. Int. Ed. 2006, 45, 1435-1439.
221. Genin, M.J.; Allwine, D.A.; Anderson, D.J.; Barbachyn, M.R.; Emmert, D.E.; Garmon, S.A.; Graber, D.R.; Grega, K.C.; Hester, J.B.; Hutchinson, D.K.; et al. Substituent Effects on the Antibacterial Activity of Nitrogen-Carbon- Linked (Azolylphenyl)oxazolidinones with Expanded Activity Against the Fastidious Gram-Negative Organisms Haemophilus influenzae and Moraxella catarrhalis. J. Med. Chem. 2000, 43, 953-970.
222. Pereira, D.; Fernandes, P. Synthesis and antibacterial activity of novel 4-aryl-[1,2,3]-triazole containing macrolides. Bioorg. Med. Chem. Lett. 2011, 21, 510-513.
223. Zhou, C.H.; Wang, Y. Recent researches in triazole compounds as medicinal drugs. Curr. Med. Chem. 2012, 19, 239-280.
224. Angell, Y.L.; Burgess, K. Peptidomimetics via copper-catalyzed azide-alkyne cycloadditions. Chem. Soc. Rev. 2007, 36, 1674-1689.
225. Empting, M.; Avrutina, O.; Meusinger, R.; Fabritz, S.; Reinwarth, M.; Biesalski, M.; Voigt, S.; Buntkowsky, G.; Kolmar, H. "Triazole Bridge": Disulfide-Bond Replacement by Ruthenium- Catalyzed Formation of 1,5-Disubstituted 1,2,3-Triazoles. Angew. Chem. Int. Ed. 2011, 50, 5207-5211.
226. Hu, T.S.; Tannert, R.; Arndt, H.D.; Waldmann, H. Solid-phase based synthesis of jasplakinolide analogs by intramolecular azide-alkyne cycloadditions. Chem. Commun. 2007, 2007, 3942-3944.
227. Turner, R.A.; Oliver, A.G.; Lokey, R.S. Click chemistry as a macrocyclization tool in the solid-phase synthesis of small cyclic peptides. Org. Lett. 2007, 9, 5011-5014.
228. Chouhan, G.; James, K. Efficient Construction of Proline-Containing β-Turn Mimetic Cyclic Tetrapeptides via CuAAC Macrocyclization. Org. Lett. 2013, 15, 1206-1209.
229. Moses, J.E.; Moorhouse, A.D. The growing applications of click chemistry. Chem. Soc. Rev. 2007, 36, 1249-1262.
230. Bogdan, A.R.; James, K. Synthesis of 5-Iodo-1,2,3-triazole-Containing Macrocycles Using Copper Flow Reactor Technology. Org. Lett. 2011, 13, 4060-4063.
231. Nahrwold, M.; Bogner, T.; Eissler, S.; Verma, S.; Sewald, N. "Clicktophycin-52": A Bioactive Cryptophycin-52 Triazole Analogue. Org. Lett. 2010, 12, 1064-1067.
232. Zhang, J.; Kemmink, J.; Rijkers, D.T.S.; Liskamp, R.M.J. Cu(I)- and Ru(II)-Mediated "Click" Cyclization of Tripeptides Toward Vancomycin-Inspired Mimics. Org. Lett. 2011, 13, 3438-3441.
233. Haridas, V.; Lal, K.; Sharma, Y.K.; Upreti, S. Design, Synthesis, and Self-Assembling Properties of Novel Triazolophanes. Org. Lett. 2008, 10, 1645-1647.
234. Bahulayan, D.; Arun, S. An easy two step synthesis of macrocyclic peptidotriazoles via a four-component reaction and copper catalyzed intramolecular azide-alkyne [3+2] click cycloaddition. Tetrahedron Lett. 2012, 53, 2850-2855.
235. Holub, J.M.; Kirshenbaum, K. Tricks with clicks: Modification of peptidomimetic oligomers via copper-catalyzed azide-alkyne [3 + 2] cycloaddition. Chem. Soc. Rev. 2010, 39, 1325-1337.
236. Ingale, S.; Dawson, P.E. On Resin Side-Chain Cyclization of Complex Peptides Using CuAAC. Org. Lett. 2011, 13, 2822-2825.
237. Ajay, A.; Sharma, S.; Gupt, M.P.; Bajpai, V.; Kumar, B.; Kaushik, M.P.; Konwar, R.; Ampapathi, R.S.; Tripathi, R.P. Diversity Oriented Synthesis of Pyran Based Polyfunctional Stereogenic Macrocyles and Their Conformational Studies. Org. Lett. 2012, 14, 4306-4309.