Functionalisation of Macroheterocycles with Preserving and Changing Their Sizes

G. Yu. Ishmuratov,^@ M. P. Yakovleva, V. A. Vydrina, М. А. Shutova, N. M. Ishmuratova, and A. G. Tolstikov

Ufa Institute of Chemistry, Russian Academy of Sciences, 450054 Ufa, Russian Federation

^@Corresponding author E-mail: insect@anrb.ru

DOI: 10.6060/mhc161066i

Macroheterocycles 2017 10(3) 345-379

This review presents methods for functionalisation of macroheterocycles occurring both with preservation and alteration of their core. It is shown that the most common methods do not affect the main ring. While functionalisation of macroheterocycles accompanied by both a decrease and an increase of their size is less common, the examples given in the literature indicate the prospects of macroheterocycle functionalisation by described methods in direct synthesis of substances for different purposes: pharmacologically active compounds, selective ligands for various (mainly transient and rare-earth) metals, odorants, etc.

References:

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1. Ishmuratov G.Yu., Yakovleva M.P., Mingaleeva G.R., Tolstikov A.G. Macroheterocycles 2011, 4, 270.
https://doi.org/10.6060/mhc2011.4.06

2. Ishmuratov G.Yu., Yakovleva M.P., Vydrina V.A., Shakhanova O.O., Ishmuratova N.M., Tolstikov A.G. Macroheterocycles 2012, 5, 212.
https://doi.org/10.6060/mhc2012.120361i

3. Denat F., Brandes S., Guilard R. Synlett. 2000, 561.
https://doi.org//10.1055/s-2000-6589

4. Shen G., Wang M., Welch T.R., Blagg B.S.J. J. Org. Chem. 2006, 71, 7618.
https://doi.org/10.1021/jo061054f

5. Sung M.J., Lee H.I., Lee H.B., Cha J.K. J. Org. Chem. 2003, 68, 2205.
https://doi.org/10.1021/jo026914g

6. Kulikov O.V., Pavlovsky V.I., Andronati S.A. Chem. Heterocycl. Compd. 2005, 41, 1447.
https://doi.org/10.1007/s10593-006-0022-5

7. Palomo С., Oiarbide M., Garcia J.M., Gonzάlez A., Pazos R., Odriozola J.M., Bañuelos P., Tello M., Linden A. J. Org. Chem. 2004, 69, 4126.
https://doi.org/10.1021/jo0497499

8. Dinh T.Q., Smith C.D., Armstrong R.W. J. Org. Chem. 1997, 62, 790.
https://doi.org/10.1021/jo962180u

9. Llàcer E., Urpi F., Vilarrasa J. Org. Lett. 2009, 11, 3198.
https://doi.org/10.1021/ol901030f

10. Nantermet P.G., Selnick H.G. Tetrahedron Lett. 2003, 44, 2401.
https://doi.org/10.1016/S0040-4039(03)00216-8

11. Krishna P.R., Anitha K. Tetrahedron Lett. 2011, 52, 4546.
https://doi.org/10.1016/j.tetlet.2011.06.087

12. Gregoliński J., Ślepokura K., Paćkowski T., Lisowski J. Org. Lett. 2014, 16, 4372.
https://doi.org/10.1021/ol501602f

13. Romo D., Rzasa R.M., Shea H.A., Park K., Langenhan J.M., Sun L., Akhiezer A., Liu J.O. J. Am. Chem. Soc. 1998, 120, 12237.
https://doi.org/10.1021/ja981846u

14. Fürstner A., Guth O., Rumbo A., Seidel G. J. Am. Chem. Soc. 1999, 121, 11108.
https://doi.org/10.1021/ja992074k

15. Wipf P., Graham T.H. J. Am. Chem. Soc. 2004, 126, 15346.
https://doi.org/10.1021/ja0443068

16. Kraft P., Berthold C. Synthesis. 2008, 4, 0543.
https://doi.org/10.1055/s-2008-1032135

17. Jakubec P., Kyle A.F., Calleja J., Dixon D.J. Tetrahedron Lett. 2011, 52, 6094.
https://doi.org/10.1016/j.tetlet.2011.09.016

18. Lehmann J., Tochtermann W. Tetrahedron. 1999, 55, 2639.
https://doi.org/10.1016/S0040-4020(99)00041-1

19. Yoshida H., Hiratani K., Ogihara T., Kobayashi Y., Kinbara K., Saigo K. J. Org. Chem. 2003, 68, 5812.
https://doi.org/10.1021/jo0340298

20. Gong W.-t., Hiratani K., Lee S.S. Tetrahedron. 2008, 64, 11007.
https://doi.org/10.1016/j.tet.2008.10.002

21. Gong W.-t., Hiratani K., Oba T., Ito S. Tetrahedron Lett. 2007, 48, 3073.
https://doi.org/10.1016/j.tetlet.2007.02.097

22. Drandarov K., Guggisberg A., Hesse M. Helv. Chim. Acta. 2002, 85, 979.
https://doi.org/10.1002/1522-2675(200204)85:4<979::AID-HLCA979>3.0.CO;2-F

23. Burguete M.I., López-Diago L., Garcia-Espaňa E., Galindo F., Luis S.V., Miravet J.F., Sroczynski D. J. Org. Chem. 2003, 68, 10169.
https://doi.org/10.1021/jo0353381

24. Dimitrov V., Geneste H., Guggisberg A., Hesse M. Helv. Chim. Acta. 2001, 84, 2108.
https://doi.org/10.1002/1522-2675(20010711)84:7<2108::AID-HLCA2108>3.0.CO;2-G

25. Guggisberg A., Drandarov K., Hesse M. Helv. Chim. Acta. 2001, 83, 3035.
https://doi.org/10.1002/1522-2675(20001108)83:11<3035::AID-HLCA3035>3.0.CO;2-P

26. Hajj F.E., Sebki G., Patinec V., Marchivie M., Triki S., Handel H., Yefsah S., Tripier R., Gómez-Garcįa C.J., Coronado E. Inorg. Chem. 2009, 48, 10416.
https://doi.org/10.1021/ic9012476

27. Camus N., Halime Z., Le Bris N., Bernard H., Platas-Iglesias C., Tripier R. J. Org. Chem. 2014, 79, 1885.
https://doi.org/10.1021/jo4028566

28. Long N.J., Parker D.G., Speyer P.R., White A.J.P., Williams D.J. J. Chem. Soc., Perkin Trans I. 1999, 1621.
https://doi.org/10.1039/a903318a

29. Alder R.W., Mowlam R.W., Vachon D.J., Weisman G.R. J. Chem. Soc., Chem. Commun. 1992, 507.
https://doi.org/10.1039/c39920000507

30. Pulacchini S., Watkinson M. Eur. J. Org. Chem. 2001, 4233.
https://doi.org/10.1002/1099-0690(200111)2001:22<4233::AID-EJOC4233>3.0.CO;2-L

31. Fang M., Fu E., Yuan Q., Xue P., Wu Ch., Chen J. Synth. Commun. 2002, 32, 3629.
https://doi.org/10.1081/SCC-120014977

32. Choi H.-J., Bae Y.-K., Kang S.-Ch., Park Y.S., Park J.W., Kima W.-I., Bell T.W. Tetrahedron Lett. 2002, 43, 9385.
https://doi.org/10.1016/S0040-4039(02)02322-5

33. Delagrange S., Nepveu F. Tetrahedron Lett. 1999, 40, 4989.
https://doi.org/10.1016/S0040-4039(99)00875-8

34. Koyama H., Yoshino T. Bull. Chem. Soc. Jpn. 1972, 45, 481.
https://doi.org/10.1246/bcsj.45.481

35. Costa J., Delgado R., Drew M.G.B., Felix V. J. Chem. Soc., Dalton Trans. 1999, 4331.
https://doi.org/10.1039/a907512g

36. Shaw B.L. J. Am. Chem. Soc. 1975, 97, 3856.
https://doi.org/10.1021/ja00846a072

37. Richman J.E., Atkins T.J. J. Am. Chem. Soc. 1974, 96, 2268.
https://doi.org/10.1021/ja00814a056

38. Hiraoka M. Crown compounds. Characteristics and application / transl. from English. Moscow: World, 1986. 363 p.
http://dx.doi.org/10.1070/RC1992v061n05ABEH000958

39. Castries A., Escande A., Fensterbank H., Magnier E., Marrot J., Larpent C. Tetrahedron. 2007, 63, 10330.
https://doi.org/10.1016/j.tet.2007.07.067

40. Prasad J.S., Okuniewicz F.J., Delaney E.J., Dischino D.D. J. Chem. Soc. Perkin Trans I. 1991, 3329.
https://doi.org/10.1039/P19910003329

41. Siaugue J.-M., Segat-Dioury F., Favre-Réguillon A., Madic Ch., Foos J., Guy A. Tetrahedron Lett. 2000, 41, 7443.
https://doi.org/10.1016/S0040-4039(00)01272-7

42. Siaugue J.-M., Segat-Dioury F., Sylvestre I., Favre-Réguillon A., Foos J., Madic Ch., Guy A. Tetrahedron. 2001, 57, 4713.
https://doi.org/10.1016/S0040-4020(01)00328-3

43. Balakrishnan K.P., Omar H.A.A., Moore P., Alcock N.W., Pike G.A. J. Chem. Soc. Dalton Trans. 1990, 2965.
https://doi.org/10.1039/dt9900002965

44. Dioury F., Sylvestre I., Siaugue J.M., Wintgens V., Ferroud C., Favre-Reguillon A., Foos J., Guy A. Eur. J. Org. Chem. 2004, 4424.
https://doi.org/10.1002/ejoc.200400264

45. Lázár I. Tetrahedron Lett. 1999, 40, 381.
https://doi.org/10.1016/S0040-4039(98)02317-X

46. Oppolzer W., Radinov R.N. J. Am. Chem. Soc. 1993, 115, 1593.
https://doi.org/10.1021/ja00057a064

47. Lebel H., Marcoux J.-F., Molinaro C., Charette A.B. Chem. Rev. 2003, 103, 977.
https://doi.org/10.1021/cr010007e

48. Lee D., Sello J.K., Schreiber S.L. J. Am. Chem. Soc. 1999, 121, 10648.
https://doi.org/10.1021/ja992658m

49. Schreiber S.L., Sammakia T., Hulin B., Schulte G. J. Am. Chem. Soc. 1986, 108, 2106.
https://doi.org/10.1021/ja00268a070

50. Bräse S., Encinas A., Keck J., Nising C.F. Chem. Rev. 2009, 109, 3903.
https://doi.org/10.1021/cr050001f

51. Meng D., Bertinato P., Balog A., Su D.-S., Kamenecka T., Sorensen E.J., Danishefsky S.J. J. Am. Chem. Soc. 1997, 119, 10073.
https://doi.org/10.1021/ja971946k

52. Zhu Y., Wang Q., Cornwall R.G., Shi Y. Chem. Rev. 2014, 114, 8199.
https://doi.org/10.1021/cr500064w

53. Ghosh P., Zhang Y., Emge T.J., Williams L.J. Org. Lett. 2009, 11, 4402.
https://doi.org/10.1021/ol901755a

54. Lu L., Zhang W., Nam S., Horne D.A., Jove R., Carter R.G. J. Org. Chem. 2013, 78, 2213.
https://doi.org/10.1021/jo3026077

55. Lu L., Zhang W., Carter R.G. J. Am. Chem. Soc. 2008, 130, 7253.
https://doi.org/10.1021/ja803012n

56. Volchkov I., Lee D. J. Am. Chem. Soc. 2013, 135, 5324.
https://doi.org/10.1021/ja401717b

57. Sierra M.A., Pellico D., Gómez-Gallego M., Mancheňo M.J., Torres R. J. Org. Chem. 2006, 71, 8787.
https://doi.org/10.1021/jo0614689

58. Pattenden G., Ashweek N.J., Baker-Glenn C.A.G., Walker G.M., Yee J.G.K. Angew. Chem. Int. Ed. 2007, 46, 4359.
https://doi.org/10.1002/anie.200700459

59. Nicolaou K.C., Schlawe D., Kim D.W., Longbottom D.A., de Noronha R.G., Lizos D.E., Manam R.R., Faulkner D. J. Chem. Eur. J. 2005, 11, 6197.
https://doi.org/10.1002/chem.200500624

60. Uchiro H., Kato R., Arai Y., Hasegawa M., Kobayakawa Y. Org. Lett. 2011, 13, 6268.
https://doi.org/10.1021/ol202748e

61. Pattenden G., Winne J.M. Tetrahedron Lett. 2010, 51, 5044.
https://doi.org/10.1016/j.tetlet.2010.07.102

62. Yamada H., Takahashi T., Kanda Y., Saitoh Y., Fukuyama T. Heterocycles. 1996, 43, 267.
https://doi.org/10.3987/COM-95-7274

63. Kanda Y., Fukuyama T. J. Am. Chem. Soc. 1993, 115, 8451.
https://doi.org/10.1021/ja00071a066

64. Kusebauch B., Scherlach K., Kirchner H., Dahse H.-M., Hertweck C. Chem. Med. Chem. 2011, 6, 1998.
https://doi.org/10.1002/cmdc.201100319

65. Cui Y., Balachandran R., Day B.W., Floreancig P.E. J. Org. Chem. 2012, 77, 2225.
https://doi.org/10.1021/jo2023685

66. Barrett A.G.M., Hennessy A.J., Le Vézouët R., Procopiou P.A., Seale P.W., Stefaniak S., Upton R.J., White A.J.P., Williams D.J. J. Org. Chem. 2004, 69, 1028.
https://doi.org/10.1021/jo0352629

67. Yang B., Zőllner T., Gebhardt P., Mőllmann U., Miller M.J. Org. Biomol. Chem. 2010, 8, 691.
https://doi.org/10.1039/B922450E

68. Meyers A.I., Roland D.M., Comins D.L., Henning R., Fleming M.P., Shimizu K. J. Am. Chem. Soc. 1979, 101, 4732.
https://doi.org/10.1021/ja00510a051

69. Rivera D.G., Wessjohann L.A. J. Am. Chem. Soc. 2009, 131, 3721.
https://doi.org/10.1021/ja809005k

70. Morisaki Y., Gon M., Sasamori T., Tokitoh N., Chujo Y. J. Am. Chem. Soc. 2014, 136, 3350.
https://doi.org/10.1021/ja412197j

71. Nicolaou K.C., Safina B.S., Zak M., Estrada A.A., Lee S.H. Angew. Chem. Int. Ed. 2004, 43, 5087.
https://doi.org/10.1002/anie.200461340

72. Nicolaou K.C., Zak M., Safina B.S., Lee S.H., Estrada A.A. Angew. Chem. Int. Ed. 2004, 43, 5092.
https://doi.org/10.1002/anie.200461341

73. McCauley J.A., Rudd M.T., Nguyen K.T., McIntyre C.J., Romano J.J., Bush K.J., Varga S.L., Ross C.W., Carroll S.S., DiMuzio J., Stahlhut M.W., Olsen D.B., Lyle T.A., Vacca J.P., Liverton N.J. Angew. Chem. Int. Ed. 2008, 47, 9104.
https://doi.org/10.1002/anie.200803298

74. Takizawa T., Watanabe K., Narita K., Kudo K., Oguchi T., Abe H., Katoh T. Heterocycles. 2008, 76, 275.
https://doi.org/10.3987/COM-07-S(N)5

75. Yurek-George A., Habens F., Brimmell M., Packham G., Ganesan A. J. Am. Chem. Soc. 2004, 126, 1030.
https://doi.org/10.1021/ja039258q

76. Li K.W., Wu J., Xing W., Simon J.A. J. Am. Chem. Soc. 1996, 118, 7237.
https://doi.org/10.1021/ja9613724

77. Yurek-George A., Cecil A.R.L., Mo A.H.K., Wen S., Rogers H., Habens F., Maeda S., Yoshida M., Packham G., Ganesan A. J. Med. Chem. 2007, 50, 5720.
https://doi.org/10.1021/jm0703800

78. Li W., Schlecker A., Ma D. Chem. Commun. 2010, 46, 5403.
https://doi.org/10.1039/c0cc00629g

79. Wen S., Packham G., Ganesan A. J. Org. Chem. 2008, 73, 9353.
https://doi.org/10.1021/jo801866z

80. Chen Y., Gambs C., Abe Y., Wentworth Jr. P., Janda K.D. J. Org. Chem. 2003, 68, 8902.
https://doi.org/10.1021/jo034765b

81. Greshock T.J., Johns D.M., Noguchi Y., Williams R.M. Org. Lett. 2008, 10, 613.
https://doi.org/10.1021/ol702957z

82. Bowers A.A., Greshock T.J., West N., Estiu G., Schreiber S.L., Wiest O., Williams R.M., Bradner J.E. J. Am. Chem. Soc. 2009, 131, 2900.
https://doi.org/10.1021/ja807772w

83 Kurosawa W., Kan T., Fukuyama T. J. Am. Chem. Soc. 2003, 125, 8112.
https://doi.org/10.1021/ja036011k

84. Kurosawa W., Kobayashi H., Kan T., Fukuyama T. Tetrahedron. 2004, 60, 9615.
https://doi.org/10.1016/j.tet.2004.06.144

85. Wang Q.-Q., Wang D.-X., Ma H.-W., Wang M.-X. Org. Lett. 2006, 8, 5967.
https://doi.org/10.1021/ol062441e

86. Shi Zh., Wang J.-h. Synth. Commun. 1997, 27, 2235.
https://doi.org/10.1080/00397919708003376

87. Salorinne K., Nissinen M. Org. Lett. 2006, 8, 5473.
https://doi.org/10.1021/ol062138d

88. Boschetti F., Denat F., Espinosa E., Tabard A., Dory Y., Guilard R. J. Org. Chem. 2005, 70, 7042.
https://doi.org/10.1021/jo050306u

89. Chartres J.D., Groth A.M., Lindoy L.F., Lowe M.P., Meehan G.V. J. Chem. Soc., Perkin Trans I. 2000, 3444.
https://doi.org/10.1039/b004797j

90. Chuburu F., Le Baccon M., Handel H. Tetrahedron. 2001, 57, 2385.
https://doi.org/10.1016/S0040-4020(01)00115-6

91. Konig B., Pelka M., Subat M., Dix I., Jones P.G. Eur. J. Org. Chem. 2001, 1943.
https://doi.org/10.1002/1099-0690(200105)2001:10<1943::AID-EJOC1943>3.0.CO;2-O

92. Averin A.D., Shukhaev A.V., Buryak A.K., Denat F., Guilard R., Beletskaya I.P. Macroheterocycles 2009, 2, 281.
https://doi.org/10.6060/mhc2009.3-4.281

93. Gaudinet-Hamann B., Zhu J., Fensterbank H., Larpent C. Tetrahedron Lett. 1999, 40, 287.
https://doi.org/10.1016/S0040-4039(98)02398-3

94. Lukyanenko N.G., Pastushok V.N., Lyapunov A.Yu., Onys'ko P.P., Sinitsa A.D., Povolotsky M.I., Shishkin O.V., Zubatyk R.I. Macroheterocycles 2009, 1, 11.
https://doi.org/10.6060/mhc2009.1.11

95. Brugel T.A., Hegedus L.S. J. Org. Chem. 2003, 68, 8409.
https://doi.org/10.1021/jo030183i

96. Achmatowicz M., Hegedus L.S., David S. J. Org. Chem. 2003, 68, 7661.
https://doi.org/10.1021/jo0301393

97. Denat F., Lacour S., Brandès S., Guilard R. Tetrahedron Lett. 1997, 38, 4417.
https://doi.org/10.1016/S0040-4039(97)00944-1

98. Develay S., Tripier R., Chuburu F., Le Baccon M., Handel H. Eur. J. Org. Chem. 2003, 3047.
https://doi.org/10.1002/ejoc.200300188

99. Tripier R., Develay S., Le Baccon M., Chuburu F., Michaud F., Handel H. New J. Chem. 2004, 28, 173.
https://doi.org/10.1039/b310074j

100. Bernier N., Allali M., Tripier R., Conan F., Patinec V., Develay S., Le Baccon M., Handel H. New J. Chem. 2006, 30, 435.
https://doi.org/10.1039/b515150c

101. Pandya D.N., Kim J.Y., Park J.Ch., Lee H., Phapale P.B., Kwak W., Choi T.H., Cheon G.J., Yoon Y.-R., Yoo J. Chem. Commun. 2010, 46, 3517.
https://doi.org/10.1039/b925703a

102. Kobelev S.M., Averin A.D., Buryak A.K., Denat F., Guilard R., Beletskaya I.P. Heterocycles. 2011, 82, 1447.
https://doi.org/10.3987/COM-10-S(E)98

103. Averin A.D., Shukhaev A.V., Buryak A.K., Denat F., Guilard R., Beletskaya I.P. Tetrahedron Lett. 2008, 49, 3950.
https://doi.org/10.1016/j.tetlet.2008.04.045

104. Kobelev S.M., Averin A.D., Buryak A.K., Savelyev E.N., Orlinson B.S., Butov G.M., Novakov I.A., Denat F., Guilard R. Beletskaya I.P. Arkivok, 2012, vii, 196.
http://dx.doi.org/10.3998/ark.5550190.0013.713

105. Kobelev S.M., Averin A.D., Buryak A.K., Denat F., Guilard R., Beletskaya I.P. Macroheterocycles 2014, 7, 28.
https://doi.org/10.6060/mhc140484a

106. Carel G., Saponar A., Saffon N., Vedrenne M., Massou S., Nemese G., Rima G., Madec D., Castel A. Tetrahedron. 2014, 70, 5650.
https://doi.org/10.1016/j.tet.2014.06.082

107. Kobelev S.M., Averin A.D., Maloshitskaya O.A., Denat F., Guilard R., Beletskaya I.P. Macroheterocycles 2012, 5, 389.
https://doi.org/10.6060/mhc2012.121102a

108. Pederson A.M.-P., Ward E.M., Schoonover D.V., Slebodnick C., Gibson H.W. J. Org. Chem. 2008, 73, 9094.
https://doi.org/10.1021/jo801886x

109. Schill G. Catenanes, Rotaxanes, and Knots(transl. Eng.) (Kostyanovsky R.G., Ed), Moscow: World, 1973. 211 p.

110. Watanabe N., Ikari Y., Kihara N., Takata T. Macromolecules. 2004, 37, 6663.
https://doi.org/10.1021/ma048782u

111. Watanabe N., Kihara N., Takata T. Org. Lett. 2001, 3, 3519.
https://doi.org/10.1021/ol016586r

112. Fuller A.-M.L., Leigh D.A., Lusby P.J., Slawin A.M.Z., Walker D.B. J. Am. Chem. Soc. 2005, 127, 12612.
https://doi.org/10.1021/ja053005a

113. Kawasaki H., Kihara N., Takata T. Chem. Lett. 1999, 28, 1015.
https://doi.org/10.1246/cl.1999.1015

114. Kihara N., Motoda S., Yokozawa T., Takata T. Org. Lett. 2005, 7, 1199.
https://doi.org/10.1021/ol047639i

115. Tachibana Y., Kawasaki H., Kihara N., Takata T. J. Org. Chem. 2006, 71, 5093.
https://doi.org/10.1021/jo0601563

116. Kihara N., Shin J.I., Ohga Y., Takata T. Chem. Lett. 2001, 30, 592.
https://doi.org/10.1246/cl.2001.592

117. Kihara N., Nakakoji N., Takata T. Chem. Lett. 2002, 31, 924.
https://doi.org/10.1246/cl.2002.924

118. Furusho Y., Oku T., Hasegawa T., Tsuboi A., Kihara N., Takata T. Chem. Eur. J. 2003, 9, 2895.
https://doi.org/10.1002/chem.200204644

119. Furusho Y., Sasabe H., Natsui D., Murakawa K.-i., Takata T., Harada T. Bull. Chem. Soc. Jpn. 2004, 77, 179.
https://doi.org/10.1246/bcsj.77.179

120. Hirose K., Nishihara K., Harada N., Nakamura Y., Masuda D., Araki M., Tobe Y. Org. Lett. 2007, 9, 2969.
https://doi.org/10.1021/ol070999w

121. Furusho Y., Matsuyama T., Takata T., Moriuchi T., Hirao T. Tetrahedron Lett. 2004, 45, 9593.
https://doi.org/10.1016/j.tetlet.2004.10.152

122. Fuller A.-M., Leigh D.A., Lusby P.J., Oswald I.D.H., Parsons S., Walker D.B. Angew. Chem. Int. Ed. 2004, 43, 3914.
https://doi.org/10.1002/anie.200353622

123. Hung W.-C., Wang L.-Y., Lai C.-C., Liu Y.-H., Peng S.-M., Chiu S.-H. Tetrahedron Lett. 2009, 50, 267.
https://doi.org/10.1016/j.tetlet.2008.10.153

124. Harrowven D.C., Woodcock T., Howes P.D. Angew. Chem. Int. Ed. 2005, 44, 3899.
https://doi.org/10.1002/anie.200500466

125. Trost B.M., Dong G. J. Am. Chem. Soc. 2010, 132, 16403.
https://doi.org/10.1021/ja105129p

126. Brewitz L., Llaveria J., Yada A., Fürstner A. Chem. Eur. J. 2013, 19, 4532.
https://doi.org/10.1002/chem.201204551

127. Green A.P., Lee A.T.L., Thomas E.J. Chem. Commun. 2011, 47, 7200.
https://doi.org/10.1039/c1cc12332g

128. Phoenix S., Reddy M.S., Deslongchamps P. J. Am. Chem. Soc. 2008, 130, 13989.
https://doi.org/10.1021/ja805097s

129. Takao K.-i., Munakata R., Tadano K.-i. Chem. Rev. 2005, 105, 4779.
https://doi.org/10.1021/cr040632u

130. Bélanger G., Deslongchamps P. Org. Lett. 2000, 2, 285.
https://doi.org/10.1021/ol990341l

131. Bélanger G., Deslongchamps P. J. Org. Chem. 2000, 65, 7070.
https://doi.org/10.1021/jo0007635

132. Song Q., Lebeis C.W., Shen X., Ho D.M., Pascal R.A. J. Am. Chem. Soc. 2005, 127, 13732.
https://doi.org/10.1021/ja0541985

133. González I., Pla-Quintana A., Roglans A., Dachs A., Solá M., Parella T., Farjas J., Roura P., Lloveras V., Vidal-Gancedo J. Chem. Commun. 2010, 46, 2944.
https://doi.org/10.1039/b926497c

134. Torrent A., González I., Pla-Quintana A., Roglans A., Moreno-Maňas M., Parella T., Benet-Buchholz J. J. Org. Chem. 2005, 70, 2033.
https://doi.org/10.1021/jo048056p

135. Xu Y., Smith M.D., Krause J.A., Shimizu L.S. J. Org. Chem. 2009, 74, 4874.
https://doi.org/10.1021/jo900443e

136. Ciesielski J., Cariou K., Frontier A.J. Org. Lett. 2012, 14, 4082.
https://doi.org/10.1021/ol3017116

137. Ciesielski J., Gandon V., Frontier A.J. J. Org. Chem. 2013, 78, 9541.
https://doi.org/10.1021/jo4007514

138. Fu H., Marquez S., Gu X., Katz L., Myles D.C. Bioorg. Med. Chem. Lett. 2006, 16, 1259.
https://doi.org/10.1016/j.bmcl.2005.11.061

139. Pavlović D., Mutak S. J. Med. Chem. 2010, 53, 5868.
https://doi.org/10.1021/jm100711p

140. Schwochert J., Pye C., Ahlbach C., Abdollahian Y., Farley K., Khunte B., Limberakis C., Kalgutkar A.S., Eng H., Shapiro M.J., Mathiowetz A.M., Price D.A., Liras S., Lokey R.S. Org. Lett. 2014, 16, 6088.
https://doi.org/10.1021/ol503170b

141. Ognyanov V.I., Hesse M. Helv. Chim. Acta. 1989, 72, 1522.
https://doi.org/10.1002/hlca.19890720714

142. Koch T., Hesse M. Helv. Chim. Acta. 1994, 77, 819.
https://doi.org/10.1002/hlca.19940770321

143. Heerklotz J.A., Fu C., Linden A., Hesse M. Helv. Chim. Acta. 2000, 83, 1809.
https://doi.org/10.1002/1522-2675(20000809)83:8<1809::AID-HLCA1809>3.0.CO;2-L

144. Koch T., Ognyanov V.I., Hesse M. Helv. Chim. Acta. 1992, 75, 62.
https://doi.org/10.1002/hlca.19920750104

145. Antonov V.C., Aghajanian Ts.E., Telesnina T.R., Shemyakin M.M. Russ. J. Gen. Chem. 1965, 35, 2231.

146. Antonov V.C., Margulyan V.S., Shemyakin M.M. Russ. J. Gen. Chem. 1969, 39, 1597.

147. Antonov V.K., Shkrob A.M., Shchelokov V.I., Shemyelcin Y.Y. Tetrahedron Lett. 1963, 1353.
https://doi.org/10.1016/S0040-4039(01)90832-9

148. Lee Y.-S., Jung J.-W., Kim S.-H., Jung J.-K., Paek S.-M., Kim N.-J., Chang D.-J., Lee J., Suh Y.-G. Org. Lett. 2010, 12, 2040.
https://doi.org/10.1021/ol100521v

149. Williams A.S. Synthesis. 1999, 1707.

https://doi.org/10.1055/s-1999-3581

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Functionalisation of Macroheterocycles with Preserving and Changing Their Sizes

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