Diversity-oriented approach to macrocyclic cyclophane derivatives via ring-closing metathesis

Synlett

Volumn 23, Issue 15, 2012, Pages 2183-2188

  Kotha, Sambasivarao ^a   Shirbhate, Mukesh E ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY BOMBAY   (India)

Author keywords

alkylation; macrocycles; oxidation; paracyclophane; ring closing metathesis

Indexed keywords

CYCLOPHANE DERIVATIVE; LONGITHORONE C; PARACYCLOPHANE DERIVATIVE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; ISOMERISM; RING CLOSING METATHESIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 84866055532     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0032-1317020     Document Type: Article

References (73)

1. Fu X, Hossain MB, van der Helm D, Schmitz FJ. J. Am. Chem. Soc.: 1994; 116 12125
2. Fu X, Hossain MB, Schmitz FJ, van der Helm D. J. Org. Chem.: 1997; 62 3810
3. Fu X, Ferreira ML, Schmitz FJ. J. Nat. Prod.: 1999; 62 1306
4. Davis RA, Carroll AR, Quinn RJ. J. Nat. Prod.: 1999; 62 158
5. Davis RA, Carroll AR, Watters D, Quinn RJ. Nat. Prod. Res., Part B: 2006; 20 1277
6. Layton ME, Morales CA, Shair MD. J. Am. Chem. Soc.: 2002; 124 773
7. Morales CA, Layton ME, Shair MD. Proc. Natl. Acad. Sci. U.S.A.: 2004; 101 12036
8. Fürstner A. Angew. Chem. Int. Ed.: 2000; 39 3012
9. Grubbs RH. Handbook of Metathesis. Vol. 1-3 Wiley-VCH Verlag GmbH & Co. KGaA Weinheim: 2003
10. Castarlenas R, Fischmeister C, Bruneau C, Dixneuf PH. J. Mol. Catal. A: Chem.: 2004; 213 31
11. Mori M. J. Mol. Catal. A: Chem.: 2004; 213 73
12. Grubbs RH. Tetrahedron: 2004; 60 7117
13. Nicolaou KC, Bulger PG, Sarlah D. Angew. Chem. Int. Ed.: 2005; 44 4490
14. Astruc D. New J. Chem.: 2005; 29 42
15. Schrock RR. Angew. Chem. Int. Ed.: 2006; 45 3748
16. Chauvin Y. Angew. Chem. Int. Ed.: 2006; 45 3740
17. Collins SK. J. Organomet. Chem.: 2006; 691 5122
18. Grubbs RH. Angew. Chem. Int. Ed.: 2006; 45 3760
19. Grubbs RH, Schrock RR, Fürstner A. Adv. Synth. Catal. Vol. 349 Wiley-VCH Verlag GmbH & Co. KGaA Weinheim: 2007; 1 265
20. Kotha S, Lahiri K. Synlett: 2007; 2767
21. Hoveyda AH, Zhugralin AR. Nature: 2007; 450 243
22. Clavier H, Grela K, Kirschning A, Mauduit M, Nolan SP. Angew. Chem. Int. Ed.: 2007; 46 6786
23. Kotha S, Shah V, Mandal K. Adv. Synth. Catal.: 2007; 349 1159
24. Kotha S, Meshram M, Tiwari A. Chem. Soc. Rev.: 2009; 38 2065
25. Cossy J, Arseniyadis S, Meyer C. Metathesis in Natural Product Synthesis; Strategies, Substrates and Catalysts. Wiley-VCH Verlag GmbH & Co. KGaA Weinheim: 2010
26. Grela K. Beilstein J. Org. Chem.: 2010; 6 1089
27. Kang SY, Kim JM, Lee JS, Lee J. Bioorg. Med. Chem. Lett.: 2011; 21 3759
28. Fürstner A, Langemann K. Synthesis: 1997; 792
29. Grubbs RH, Lee CW. J. Org. Chem.: 2001; 66 7155
30. Chuchuryukin AV, Dijkstra HP, Suijkerbuijk BM. J. M, Gebbink RJ. M. K, van Klink GP. M, Mills AM, Spek AL, van Koten G. Angew. Chem. Int. Ed.: 2003; 42 228
31. Gradillas A, Pérez-Castells J. Angew. Chem. Int. Ed.: 2006; 45 6086
32. Albrecht M. Yeni Fröhlich R. Synlett: 2007; 2295
33. El-Azizi Y, Zakarian JE, Bouillerand L, Schmitzer AR, Collins SK. Adv. Synth. Catal.: 2008; 350 2219
34. Diederich F, Stang PJ, Tykwinski RR. Modern Supramolecular Chemistry: Strategies for Macrocycle Synthesis. Wiley-VCH Verlag GmbH & Co. KGaA Weinheim: 2008; 29 67
35. Abell AD, Alexander NA, Aitken SG, Chen H, Coxon JM, Jones MA, McNabb SB, Muscroft-Taylor A. J. Org. Chem.: 2009; 74 4354
36. Muthusamy S, Azhagan D. Tetrahedron: 2010; 66 8196
37. Jarikote DV, Murphy PV. Eur. J. Org. Chem.: 2010; 4959
38. Bolduc P, Jacques A, Collins SK. J. Am. Chem. Soc.: 2010; 132 12790
39. Diederich F. Cyclophanes. Royal Society of Chemistry Cambridge: 1991
40. Vögtle F. Cyclophane Chemistry: Synthesis, Structures, and Reactions. John Wiley and Sons Chichester: 1993
41. Weber E. Cyclophanes. Vol. 172 Springer Verlag Berlin: 1994
42. Takemura H. Cyclophane Chemistry for the 21st Century. Research Signpost Trivandrum: 2002
43. Gleiter R, Hopf H. Modern Cyclophane Chemistry. Wiley-VCH Verlag GmbH & Co. KGaA Weinheim: 2004
44. Davis F, Higson S. Macrocycles: Construction, Chemistry and Nanotechnology Applications. John Wiley and Sons Ltd Chichester: 2011
45. Jimenez L, Diederich F. Tetrahedron Lett.: 1989; 30 2759
46. Diederich F, Lutter HD. J. Am. Chem. Soc.: 1989; 111 8438
47. Seel C, Vögtle F. Angew. Chem. Int. Ed. Engl.: 1992; 31 528
48. Newman DJ, Cragg GM, Snader KM. Nat. Prod. Rep.: 2000; 17 215
49. Fürstner A. Eur. J. Org. Chem.: 2004; 943
50. Rajakumar P, Rasheed AM. A, Rabia AI, Chamundeeswari D. Bioorg. Med. Chem. Lett.: 2006; 16 6019
51. Rajakumar P, Rasheed AM. A, Balu PM, Murugesan K. Bioorg. Med. Chem.: 2006; 14 7458
52. Driggers EM, Hale SP, Lee J, Terrett NK. Nat. Rev. Drug Discovery: 2008; 7 608
53. Huang M, Song L, Liu B. Org. Lett.: 2010; 12 2504
54. Yoshinari T, Ohmori K, Schrems MG, Pfaltz A, Suzuki K. Angew. Chem. Int. Ed.: 2010; 49 881
55. Kotha S, Krishna NG, Halder S, Misra S. Org. Biomol. Chem.: 2011; 9 5597
56. Bodwell GJ, Nandaluru PR. Isr. J. Chem.: 2012; 52 105
57. Mohan A, Sankararaman S. Isr. J. Chem.: 2012; 52 92
58. Kotha S, Halder S, Damodharan L, Pattabhi V. Bioorg. Med. Chem. Lett.: 2002; 12 1113
59. Kotha S, Behera M, Kumar RV. Bioorg. Med. Chem. Lett.: 2002; 12 105
60. Kotha S, Mandal K, Arora KK, Pedireddi VR. Adv. Synth. Catal.: 2005; 347 1215
61. Kotha S, Behera M, Shah V. Synlett: 2005; 1877
62. Kotha S, Halder S. ARKIVOC: 2005; (iii) 56
63. Kotha S, Mandal K. Eur. J. Org. Chem.: 2006; 5387
64. Kotha S, Lahiri K. Eur. J. Org. Chem.: 2007; 1221
65. Kotha S, Mandal K. Chem. Asian J.: 2009; 4 354
66. Kotha S, Chavan AS, Mobin S. J. Org. Chem.: 2012; 77 482
67. Yamazaki T, Kasatkin A, Kawanaka Y, Sato F. J. Org. Chem.: 1996; 61 2266
68. Salomon RG, Coughlin DJ, Ghosh S, Zagorski MG. J. Am. Chem. Soc.: 1982; 104 998
69. Oppolzer W, Pitteloud R, Strauss HF. J. Am. Chem. Soc.: 1982; 104 6476
70. Williams RM, Lee BH, Miller MM, Anderson OP. J. Am. Chem. Soc.: 1989; 111 1073
71. Saint-Dizier AC, Kilburn JD. Tetrahedron Lett.: 2002; 43 6201
72. Miyazawa N, Ogasawara K. Synlett: 2002; 1065
73. Grenning AJ, Tunge JA. J. Am. Chem. Soc.: 2011; 133 14785; and the references cited therein