Skip to main content
SpringerLink
Log in

Multicomponent Syntheses of Macrocycles

  • Chapter
  • First Online:
Book cover Synthesis of Heterocycles via Multicomponent Reactions II

Part of the book series: Topics in Heterocyclic Chemistry ((TOPICS,volume 25))

Abstract

How to access efficiently the macrocyclic structure remained to be a challenging synthetic topic. Although many elegant approaches/reactions have been developed, construction of diverse collection of macrocycles is still elusive. This chapter summarized the recently emerged research area dealing with multicomponent synthesis of macrocycles, with particular emphasis on the approach named “multiple multicomponent reaction using two bifunctional building blocks”.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Log in via an institution
Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 349.00
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 449.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 449.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

References

  1. Shu Y-Z (1998) J Nat Prod 61:1053–1071

    Article  CAS  Google Scholar 

  2. Newman DJ, Cragg GM, Snader KM (2000) Nat Prod Rep 17:215–234

    Article  CAS  Google Scholar 

  3. Feliu L, Planas M (2005) Int J Pept Res Ther 11:53–97

    Article  CAS  Google Scholar 

  4. Wessjohann LA, Ruijter E, Garcia-Rivera D, Brandt W (2005) Mol Divers 9:171–186

    Article  CAS  Google Scholar 

  5. Williams DH (1996) Nat Prod Rep 13:469–477

    Article  CAS  Google Scholar 

  6. Zhu J (1999) Expert Opin Ther Pat 9:1005–1019

    Article  CAS  Google Scholar 

  7. Nicolaou KC, Boddy CNC, Bräse S, Winssinger N (1999) Angew Chem Int Ed 38:2096–2152

    Article  Google Scholar 

  8. Süssmuth RD (2002) Chembiochem 3:295–298

    Article  Google Scholar 

  9. Kessler H (1982) Angew Chem Int Ed Engl 21:512–523

    Article  Google Scholar 

  10. Toniolo C (1990) Int J Pept Protein Res 35:287–300

    Article  CAS  Google Scholar 

  11. Lambert JN, Mitchell JP, Roberts KD (2001) J Chem Soc Perkin Trans 1:471–484

    Google Scholar 

  12. Hu HT, Xu CR, Song X, Siahaan TJ (2003) J Pept Res 61:331–342

    Article  Google Scholar 

  13. Fairlie DP, Abbenante G, March DR (1995) Curr Med Chem 2:654–686

    CAS  Google Scholar 

  14. Winnik MA (1985) Acc Chem Res 18:73–79

    Article  CAS  Google Scholar 

  15. Lehn J-M (1995) Supramolecular chemstry: concepts and perspectives. Wiley-VCH, Weinheim

    Book  Google Scholar 

  16. Raymo FM, Stoddart JF (1999) Chem Rev 99:1643–1663

    Article  CAS  Google Scholar 

  17. Wang M-X (2008) Chem Commun:4541–4551

    Google Scholar 

  18. Ghadiri MR, Granja JR, Milligan RA, McRee DE, Khazanovich N (1993) Nature 366:324–327

    Article  CAS  Google Scholar 

  19. Meng Q, Hesse M (1991) In: Topics in current chemistry, vol 161, pp 107–175

    Google Scholar 

  20. Wipf P (1995) Chem Rev 95:2115–2134

    Article  CAS  Google Scholar 

  21. Zhu J (1997) Synlett:133–144

    Google Scholar 

  22. Fürstner A (2000) Angew Chem Int Ed Engl 39:3012–3043

    Article  Google Scholar 

  23. Yeung K-S, Paterson I (2002) Angew Chem Int Chem 41:4632–4653

    Article  CAS  Google Scholar 

  24. Wessjohann LA, Ruijter E (2005) Top Curr Chem 243:137–184

    CAS  Google Scholar 

  25. Nicolaou KC, Bulger PG, Sarlah D (2005) Angew Chem Int Ed Engl 44:4490–4527

    Article  CAS  Google Scholar 

  26. Hoye TR, Humpal PE, Moon B (2000) J Am Chem Soc 122:4982–4983

    Article  CAS  Google Scholar 

  27. Smith AB III, Kozmin SA, Adams CM, Paone DV (2000) J Am Chem Soc 122:4984–4985

    Article  CAS  Google Scholar 

  28. Singh Y, Sokolenko N, Kelso MJ, Gahan LR, Abbenante G, Fairlie DP (2001) J Am Chem Soc 123:333–334

    Article  CAS  Google Scholar 

  29. Zhu J, Bienaymé H (eds) (2005) Multicomponent reaction. Wiley-VCH, Weinheim

    Google Scholar 

  30. Trost BM (1995) Angew Chem Int Ed 34:259–281

    Article  CAS  Google Scholar 

  31. Wender PA, Handy S, Wright DL (1997) Chem Ind:765–769

    Google Scholar 

  32. Bienaymé H, Hulme C, Oddon G, Schmitt P (2000) Chem Eur J 6:3321–3329

    Article  Google Scholar 

  33. Posner GH (1986) Chem Rev 86:831–844

    Article  CAS  Google Scholar 

  34. Armstrong RW, Combs AP, Tempest PA, Brown SD, Keating TA (1996) Acc Chem Res 29:123–131

    Article  CAS  Google Scholar 

  35. Hulme C, Gore V (2003) Curr Med Chem 10:51–80

    Article  CAS  Google Scholar 

  36. Orru RVA, De Greef M (2003) Synthesis:1471–1499

    Google Scholar 

  37. Jacobi von Wangelin A, Neumann H, Gördes D, Klaus S, Strübing D, Beller M (2003) Chem Eur J 9:4286–4294

    Article  Google Scholar 

  38. Balme G, Bossharth E, Monteiro N (2003) Eur J Org Chem:4101–4111

    Google Scholar 

  39. Zhu J (2003) Eur J Org Chem:1133–1144

    Google Scholar 

  40. Simon C, Constantieux T, Rodriguez J (2004) Eur J Org Chem:4957–4980

    Google Scholar 

  41. Tempest P (2005) Curr Opin Drug Discov Devel 8:776–788

    CAS  Google Scholar 

  42. Wessjohann LA, Rüijter E (2005) Top Curr Chem 243:137–184

    CAS  Google Scholar 

  43. Dömling A (2006) Chem Rev 106:17–89

    Article  Google Scholar 

  44. D’Souza DM, Müller TJJ (2007) Chem Soc Rev 36:1095–1108

    Article  Google Scholar 

  45. Tejedor D, Garcia-Tellado F (2007) Chem Soc Rev 36:484–491

    Article  CAS  Google Scholar 

  46. Akritopoulou-Zane I, Djuric SW (2007) Heterocycles 73:125–147

    Article  Google Scholar 

  47. Isambert N, Lavilla R (2008) Chem Eur J 14:8444–8454

    Article  CAS  Google Scholar 

  48. El Kaim L, Grimaud L (2009) Tetrahedron 65:2153–2171

    Article  CAS  Google Scholar 

  49. Ganem B (2009) Acc Chem Res 42:463–472

    Article  CAS  Google Scholar 

  50. Arndtsen BA (2009) Chem Eur J 15:302–313

    Article  CAS  Google Scholar 

  51. Sunderhaus JD, Martin SF (2009) Chem Eur J 15:1300–1308

    Article  CAS  Google Scholar 

  52. Godineau E, Landais Y (2009) Chem Eur J 15:3044–3055

    Article  CAS  Google Scholar 

  53. Wessjohann LA, Ruijter E (2005) Mol Divers 9:159–169

    Article  CAS  Google Scholar 

  54. Wessjohann LA, Rivera DG, Vercillo OE (2009) Chem Rev 109:796–814

    Article  CAS  Google Scholar 

  55. Morokuma K (1977) Acc Chem Res 10:294–300

    Article  CAS  Google Scholar 

  56. Blankenstein J, Zhu J (2005) Eur J Org Chem:1949–1964

    Google Scholar 

  57. Dömling A, Ugi I (2000) Angew Chem Int Ed Engl 39:3168–3210

    Article  Google Scholar 

  58. Marcaccini S, Torroba T (2007) Nat Protoc 2:632–639

    Article  CAS  Google Scholar 

  59. Kehagia K, Ugi I (1995) Tetrahedron 51:9523–9530

    Article  CAS  Google Scholar 

  60. Ugi I, Steinbrückner C (1961) Chem Ber 94:2802–2814

    Article  CAS  Google Scholar 

  61. Isenring HP, Hofheinz W (1981) Synthesis:385–387

    Google Scholar 

  62. Failli A, Immer H, Götz M (1979) Can J Chem 57:3257–3261

    Article  CAS  Google Scholar 

  63. Vercillo OE, Andrade CKZ, Wessjohann LA (2008) Org Lett 10:205–208

    Article  CAS  Google Scholar 

  64. Hili R, Rai V, Yudin AK (2010) J Am Chem Soc 132:2889–2891

    Article  CAS  Google Scholar 

  65. Giovenzana GB, Tron GC, Di Paola S, Menegotto IG, Pirali T (2006) Angew Chem Int Ed 45:1099–1102

    Article  CAS  Google Scholar 

  66. Kunz H, Pfrengle W (1988) J Am Chem Soc 110:651–652

    Article  CAS  Google Scholar 

  67. Linderman RJ, Binet S, Petrich SR (1999) J Org Chem 64:336–337

    Article  CAS  Google Scholar 

  68. Ross GF, Herdtweck E, Ugi I (2002) Tetrahedron 58:6127–6133

    Article  CAS  Google Scholar 

  69. Cuny G, Gamez-Montano R, Zhu J (2004) Tetrahedron 60:4879–4885

    Article  CAS  Google Scholar 

  70. Basso A, Banfi L, Riva R, Guanti G (2005) J Org Chem 70:576–580

    Article  Google Scholar 

  71. Banfi L, Basso A, Guanti G, Merlo S, Repetto C, Riva R (2008) Tetrahedron 64:1114–1134

    Article  CAS  Google Scholar 

  72. Bonger KM, Wennekes T, Filippov DV, Lodder G, van de Marel GA, Overkleeft HS (2008) Eur J Org Chem:3678–3688

    Google Scholar 

  73. Denmark S, Fan Y (2003) J Am Chem Soc 125:7824–7825

    Google Scholar 

  74. Kusebauch U, Beck B, Messer K, Herdtweck E, Dömling A (2003) Org Lett 5:4021–4024

    Article  CAS  Google Scholar 

  75. Andreana PR, Liu CC, Schreiber SL (2004) Org Lett 6:4231–4234

    Article  CAS  Google Scholar 

  76. Wang S-X, Wang M-X, Wang D-X, Zhu J (2007) Eur J Org Chem:4076–4080

    Google Scholar 

  77. Wang S-X, Wang M-X, Wang D-X, Zhu J (2007) Org Lett 9:3615–3618

    Article  CAS  Google Scholar 

  78. Wang S-X, Wang M-X, Wang D-X, Zhu J (2008) Angew Chem Int Ed 47:388–391

    Article  CAS  Google Scholar 

  79. Yue T, Wang M-X, Wang D-X, Zhu J (2008) Angew Chem Int Ed 47:9454–9457

    Article  CAS  Google Scholar 

  80. Yue T, Wang M-X, Wang D-X, Masson G, Zhu J (2009) Angew Chem Int Ed 48:6717–6721

    Article  CAS  Google Scholar 

  81. Rivera DG, Wessjohann LA (2007) Molecules 12:1890–1899

    Article  CAS  Google Scholar 

  82. Pauvannan K (1999) Tetrahedron Lett 40:1851–1854

    Article  Google Scholar 

  83. Lee D, Sello JK, Schreiber SL (2000) Org Lett 2:709–712

    Article  CAS  Google Scholar 

  84. Fayol A, Housseman C, Sun X, Janvier P, Bienaymé H, Zhu J (2005) Synthesis:161–165

    Google Scholar 

  85. Housseman C, Zhu J (2006) Synlett:1777–1779

    Google Scholar 

  86. Dömling A, Beck B, Fuchs T, Yazbak A (2006) J Comb Chem 8:872–880

    Article  Google Scholar 

  87. Pirali T, Tron GC, Zhu J (2006) Org Lett 8:4145–4148

    Article  CAS  Google Scholar 

  88. Sun X, Janvier P, Zhao G, Bienaymé H, Zhu J (2001) Org Lett 3:877–880

    Article  CAS  Google Scholar 

  89. Janvier P, Sun X, Bienaymé H, Zhu J (2002) J Am Chem Soc 124:2560–2567

    Article  CAS  Google Scholar 

  90. Fayol A, Zhu J (2002) Angew Chem Int Ed 41:3633–3635

    Article  CAS  Google Scholar 

  91. Janvier P, Bienaymé H, Zhu J (2002) Angew Chem Int Ed 41:4291–4294

    Article  CAS  Google Scholar 

  92. Gámez-Montaño R, González-Zamora E, Potier P, Zhu J (2002) Tetrahedron 58:6351–6358

    Article  Google Scholar 

  93. Fayol A, Zhu J (2005) Org Lett 7:239–242

    Article  CAS  Google Scholar 

  94. Bonne D, Dekhane M, Zhu J (2007) Angew Chem Int Ed 46:2485–2488

    Article  CAS  Google Scholar 

  95. Touré BB, Hall DG (2009) Chem Rev 109:4439–4486

    Article  Google Scholar 

  96. Wessjohann LA, Voigt B, Rivera DG (2005) Angew Chem Int Ed 44:4785–4790

    Article  CAS  Google Scholar 

  97. Wessjohann LA, Rivera DG, Coll F (2006) J Org Chem 71:7521–7526

    Article  CAS  Google Scholar 

  98. Kreye O, Westermann B, Rivera DG, Johnson DV, Orru RVA (2006) QSAR Comb Sci 25:461–464

    Article  CAS  Google Scholar 

  99. Rivera DG, Wessjohann LA (2006) J Am Chem Soc 128:7122–7123

    Article  CAS  Google Scholar 

  100. Rivera DG, Vercillo OE, Wessjohann LA (2007) Synlett:308–312

    Google Scholar 

  101. Leon F, Rivera DG, Wessjohann LA (2008) J Org Chem 73:1762–1767

    Article  CAS  Google Scholar 

  102. Ngouansavanh T, Zhu J (2006) Angew Chem Int Ed 45:3495–3497

    Article  CAS  Google Scholar 

  103. Janvier P, Bois-Choussy M, Bienaymé H, Zhu J (2003) Angew Chem Int Ed 42:811–814

    Article  CAS  Google Scholar 

  104. Zhao G, Sun X, Bienaymé H, Zhu J (2001) J Am Chem Soc 123:6700–6701

    Article  CAS  Google Scholar 

  105. Bughin C, Zhao G, Bienaymé H, Zhu J (2006) Chem Eur J 12:1174–1184

    Article  CAS  Google Scholar 

  106. Bughin C, Masson G, Zhu J (2007) J Org Chem 72:1826–1829

    Article  CAS  Google Scholar 

  107. Pirali T, Tron G, Masson G, Zhu J (2007) Org Lett 9:5275–5278

    Article  CAS  Google Scholar 

  108. Seel C, Vogtle F (2000) Chem Eur J 6:21–24

    Article  CAS  Google Scholar 

  109. Carver FJ, Hunter CA, Shannon RJ (1994) J Chem Soc Chem Commun:1277–1280

    Google Scholar 

  110. León F, Rivera DG, Wessjohann LA (2008) J Org Chem 73:1762–1767

    Article  Google Scholar 

  111. Wessjohann LA, Rivera DG, León F (2007) Org Lett 9:4733–4736

    Article  CAS  Google Scholar 

  112. Rivera DG, Wessjohann LA (2009) J Am Chem Soc 131:3721–3732

    Article  CAS  Google Scholar 

  113. Christinat N, Scopelliti R, Severin K (2007) J Org Chem 72:2192–2200

    Article  CAS  Google Scholar 

  114. Christinat N, Scopelliti R, Severin K (2008) Angew Chem Int Ed 47:1848–1852

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles, CNRS, 91198, Gif-sur-Yvette Cedex, France

    Géraldine Masson, Luc Neuville, Carine Bughin, Aude Fayol & Jieping Zhu

Authors
  1. Géraldine Masson
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Luc Neuville
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Carine Bughin
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Aude Fayol
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Jieping Zhu
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Jieping Zhu .

Editor information

Editors and Affiliations

  1. Fac. Sciences, Dept. Chemistry &, VU University Amsterdam, De Boelelaan 1083, Amsterdam, 1081 HV, Netherlands

    Romano V. A. Orru

  2. Faculty of Sciences, Section of Synthetic &, VU University Amsterdam, Amsterdam, 1081 HV, Netherlands

    Eelco Ruijter

Rights and permissions

Reprints and permissions

Copyright information

© 2010 Springer-Verlag Berlin Heidelberg

About this chapter

Cite this chapter

Masson, G., Neuville, L., Bughin, C., Fayol, A., Zhu, J. (2010). Multicomponent Syntheses of Macrocycles. In: Orru, R., Ruijter, E. (eds) Synthesis of Heterocycles via Multicomponent Reactions II. Topics in Heterocyclic Chemistry, vol 25. Springer, Berlin, Heidelberg. https://doi.org/10.1007/7081_2010_47

Download citation

Publish with us

Policies and ethics

Search

Navigation