Application of 6,7-indole aryne cycloaddition and Pd(0)-catalyzed Suzuki-Miyaura and Buchwald-Hartwig cross-coupling reactions for the preparation of annulated indole libraries

ACS Combinatorial Science

Volumn 13, Issue 5, 2011, Pages 443-448

  Thornton, Paul D ^b   Brown, Neil ^a,b   Hill, David ^b   Neuenswander, Ben ^b   Lushington, Gerald H ^b   Santini, Conrad ^b   Buszek, Keith R ^a,b  

^a UNIVERSITY OF MISSOURI KANSAS CITY   (United States)

^b UNIVERSITY OF KANSAS   (United States)

Author keywords

aryne; Buchwald Hartwig; cycloaddition; Indole; indolyne; libraries; Suzuki Miyaura

Indexed keywords

INDOLE DERIVATIVE; ORGANOMETALLIC COMPOUND; PALLADIUM;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; MOLECULAR LIBRARY; STEREOISOMERISM; SYNTHESIS;

CATALYSIS; CHEMISTRY TECHNIQUES, SYNTHETIC; CYCLIZATION; INDOLES; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; PALLADIUM; SMALL MOLECULE LIBRARIES; STEREOISOMERISM;

EID: 80052739326     PISSN: 21568952     EISSN: None     Source Type: Journal    
DOI: 10.1021/co2000289     Document Type: Article

References (35)

1. Buszek, K. R.; Luo, D.; Kondrashov, M.; Brown, N.; Vander Velde, D. Indole-Derived Arynes and Their Diels-Alder Reactivity with Furans Org. Lett. 2007, 9, 4135-4137
2. Buszek, K. R.; Brown, N.; Luo, D. Concise Total Synthesis of (±)- cis -Trikentrin A and (±)-Herbindole A via Intermolecular Indole Aryne Cycloaddition Org. Lett. 2009, 11, 201-204
3. Brown, N.; Luo, D.; VanderVelde, D.; Yang, S.; Brassfield, A.; Buszek, K. R. Regioselective Diels-Alder Cycloadditions and Other Reactions of 4,5-, 5,6-, and 6,7-Indole Arynes Tetrahedron Lett. 2009, 50, 63-65
4. Brown, N.; Luo, D.; Decapo, J. A.; Buszek, K. R. New Synthesis of (±)-cis-Trikentrin A via Tandem Indole Aryne Cycloaddition/Negishi Reaction. Applications to Library Development Tetrahedron Lett. 2009, 50, 7113-7115
5. Garr, A. N.; Luo, D.; Brown, N.; Cramer, C. J.; Buszek, K. R.; VanderVelde, D. Experimental and Theoretical Investigations into the Unusual Regioselectivity of 4,5-, 5,6-, and 6,7-Indole Aryne Cycloadditions Org. Lett. 2010, 12, 96-99
6. Bronner, S. M.; Bahnck, K. B.; Garg, N. K. Indolynes as Electrophilic Surrogates: Fundamental Reactivity and Synthetic Applications Org. Lett. 2009, 11, 1007-1010
7. Tian, X.; Huters, A. D.; Douglas, C. J.; Garg, N. K. Concise Synthesis of the Bicyclic Scaffold of N -Methylwelwitindolinone C Isothiocyanate via an Indolyne Cyclization Org. Lett. 2009, 11, 2349-2351
8. Bronner, S. M.; Garg, N. K. Efficient Synthesis of 2-(Trimethylsilyl) phenyl Trifluoromethanesulfonate: A Versatile Precursor to o -Benzyne J. Org. Chem. 2009, 74, 8842-8843
9. Cheong, P. H.-Y.; Paton, R. S.; Bronner, S. M.; Im, G.-T. J.; Garg, N. K.; Houk, K. N. Indolyne and Aryne Distortions and Nucleophilic Regioselectivities J. Am. Chem. Soc. 2010, 132, 1267-1269
10. Im, G-Y. J.; Bronner, S. M.; Goetz, A. E.; Paton, R. S.; Cheong, P. H.-Y.; Houk, K. N.; Garg, N. K. Indolyne Experimental and Computational Studies: Synthetic Applications and Origins of Selectivities of Nucleophilic Additions J. Am. Chem. Soc. 2010, 132, 17933-17944
11. Bronner, S. M.; Goetz, A. E.; Garg, N. K. Overturning Indolyne Regioselectivities and Synthesis of Indolactam V J. Am. Chem. Soc. 2011, 133, 3832-3835
12. Nguyen, T. D.; Webster, R.; Lautens, M. Rh(I)-Catalyzed Ring-Opening of Hetaryne-Furan Diels-Alder Adducts: Rapid Access to Stereochemically Defined Heterocyclic Scaffolds Org. Lett. 2011, 13, 1370-1373
13. Brown, N.; Xie, B.; Markina, N.; VanderVelde, D.; Perchellet, J.-P. H.; Perchellet, E. M.; Crow, K. R.; Buszek, K. R. Synthesis of a Natural Product-Inspired Eight-Membered Ring Lactam Library via Ring-Closing Metathesis Bioorg. Med. Chem. Lett. 2008, 18, 4876-4879
14. Brown, N.; Gao, G.; Minatoya, M.; Xie, B.; VanderVelde, D.; Lushington, G. H.; Perchellet, J-P. H.; Perchellet, E. M.; Crow, K. R.; Buszek, K. R. Design and Synthesis of Medium-Ring Libraries Inspired by Octalactin A. A Convergent-Divergent Approach J. Comb. Chem. 2008, 10, 628-631
15. Jackson, S, K.; Kerr, M. A. Total Synthesis of (±)-Herbindole A, (±)-Herbindole B, and (±)- cis -Trikentrin A J. Org. Chem. 2007, 72, 1405-1411
16. Huntley, R. J.; Funk, R. L. Total Synthesis of (±)- cis -Trikentrin A and (±)- cis -Trikentrin B via Electrocyclic Ring Closures of 2,3-Divinylpyrrolines Org. Lett. 2006, 8, 3403-3406 (Pubitemid 44187464)
17. MacLeod, J. K.; Monahan, L. C. The Synthesis of (±)- cis -Trikentrin A Tetrahedron Lett. 1988, 29, 391-392
18. Jackson, S. K.; Banfield, S. C.; Kerr, M. A. Total Synthesis of (±)-Herbindole B and (±)- cis -Trikentrin B Org. Lett. 2005, 7, 1215-1218, and references cited therein (Pubitemid 40544084)
19. Hitotsuyanagi, Y.; Fujiki, H.; Suganuma, M.; Aimi, N.; Sakai, S.-I.; Endo, Y.; Shudo, K.; Sugimura, T. Isolation and Structure Elucidation of Teleocidin B-1, B-2, and B-4 Chem. Pharm. Bull. 1984, 32, 4233-4236 (Pubitemid 15208377)
20. Nakatsuka, S.; Matsuda, T.; Asano, O.; Terame, T.; Goto, T. Synthetic Studies on Teleocidin. I. Regioselective Introduction of 4-Amino and 7-Acyl Groups on Indole Derivative Tetrahedron Lett. 1986, 27, 4327-4330
21. Nakatsuka, S.; Masuda, T.; Goto, T. Synthetic Studies on Teleocidin. II. Synthesis of Indole Derivatives Containing the Same Substituent to Teleocidin B at 6- and 7-Positions of Indole Nucleus Tetrahedron Lett. 1986, 27, 6245-6248 (Pubitemid 17201348)
22. Nakatsuka, S.; Masuda, T.; Goto, T. Total Synthesis of (±)-Teleocidin B-3 and B-4 Tetrahedron Lett. 1987, 28, 3671-3674
23. Singh, S. B.; Ondeyka, J. G.; Jayasuriya, H.; Zink, D. L.; Ha, S. N.; Dahl-Roshak, A.; Greene, J.; Kim, J. A.; Smith, M. M.; Shoop, W.; Tkacz, J. S. Nodulisporic Acids D-F: Structure, Biological Activities, and Biogenetic Relationships J. Nat. Prod. 2004, 67, 1496-1506 (Pubitemid 39298617)
24. Smith, A. B., III; Kuerti, L.; Davulcu, A. H.; Cho, Y. S.; Ohmoto, K. Indole Diterpene Synthetic Studies: Development of a Second-Generation Synthetic Strategy for (+)-Nodulisporic Acids A and B J. Org. Chem. 2007, 72, 4611-4620 (Pubitemid 46981803)
25. Bartoli, G.; Palmieri, G.; Bosco, M.; Dalpozzo, R. The Reaction of Vinyl Grignard Reagents with 2-Substituted Nitroarenes: A New Approach to the Synthesis of 7-Substituted Indoles Tetrahedron Lett. 1989, 30, 2129-2132 (Pubitemid 19129747)
26. Bartoli, G.; Bosco, M.; Dalpozzo, R.; Palmieri, G.; Marcantoni, E. Reactivity of Nitro- and Nitroso-Arenes with Vinyl Grignard Reagents: Synthesis of 2-(Trimethylsilyl)indoles J. Chem. Soc. PT1 1991, 2757-2761
27. Bosco, M.; Dalpozzo, R.; Bartoli, G.; Palmieri, G.; Petrini, M. Mechanistic Studies on the Reaction of Nitro- and Nitrosoarenes with Vinyl Grignard Reagents J. Chem. Soc. PT2 1991, 657-663
28. Dalpozzo, R.; Bartoli, G. Bartoli Indole Synthesis Curr. Org. Chem. 2005, 9, 163-178 (Pubitemid 40089534)
29. Buszek, K. R.; Brown, N. Improved Method for the Diimide Reduction of Multiple Bonds on Solid-Supported Substrates J. Org. Chem. 2007, 72, 3125-3128 (Pubitemid 46624455)
30. Marcaurelle, L. A.; Comer, E.; Dandapani, S.; Duvall, J. R.; Gerard, B.; Kesavan, S.; Lee, M. D.; Liu, H.; Lowe, J. T.; Marie, J.-C.; Mulrooney, C. A.; Pandya, B. A.; Rowley, A.; Ryba, T. D.; Suh, B.-C.; Wei, J.; Young, D. W.; Akella, L. B.; Ross, N. T.; Zhang, Y.-L.; Fass, D. M.; Reis, S. A.; Zhao, W.-N.; Haggarty, S. J.; Palmer, M.; Foley, M. A. An Aldol-Based Build/Couple/Pair Strategy for the Synthesis of Medium- and Large-Sized Rings: Discovery of Macrocyclic Histone Deacetylase Inhibitors J. Am. Chem. Soc. 2010, 132, 16962-16976
31. SYBYL 8.0; The Tripos Associates: St. Louis, MO, 2008.
32. 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 Adv. Drug Delivery Rev. 1997, 23, 3-25 (Pubitemid 27046991)
33. Concord 8.0; The Tripos Associates: St. Louis, MO, 2008.
34. Cruciani, G.; Meniconi, M.; Carosati, E.; Zamora, I.; Mannhold, R. VOLSURF: A Tool for Drug ADME-Properties Prediction. In Methods and Principles in Medicinal Chemistry; van de Waterbeemd, H.; Lennernäs, H.; Artursson, P., Eds.; Wiley-VCH Verlag GmbH & Co.: Weinheim, Germany, 2003.
35. Pearlman, R. S.; Smith, K. M. Metric Validation and the Receptor-Relevant Subspace Concept J. Chem. Inf. Comput. Sci. 1999, 39, 28-35 (Pubitemid 129676554)