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Synthesis of 12- to 16-Membered-Ring Lactones

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Synthesis of Saturated Oxygenated Heterocycles II

Part of the book series: Topics in Heterocyclic Chemistry ((TOPICS,volume 36))

Abstract

A wide variety of natural products exhibit a macrocyclic lactone motif with a large spectrum of biological properties ranging from perfumery, over phytotoxicity, pheromone, or insecticide activity to medicinal (antibiotic, cytotoxic, antiangiogenesis) properties. These molecules feature a wide range of cyclic structures up to 60-membered rings. For this reason, the devise of new macrolactonization methods is always of general interest. The objective of this chapter is not only to present an overview of the macrolactonization of seco-acids in the total synthesis of natural products but to present other new effective procedures for the ring closure of 12- to 16-membered ring lactones.

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References

  1. Pennella F, Banks RL, Bailey GC (1968) Chem Commun (23): 1548

    Google Scholar 

  2. Mortreux A, Blanchard M (1974) J Chem Soc Chem Commun 19:786

    Google Scholar 

  3. Fürstner A, Stelzer F, Rumbo A, Krause H (2002) Chem Eur J 8(8):1856

    Google Scholar 

  4. Wengrovius JH, Sancho J, Schrock RR (1981) J Am Chem Soc 103(13):3932

    CAS  Google Scholar 

  5. Schrock RR, Clark DN, Sancho J, Wengrovius JH, Rocklage SM, Pedersen SF (1982) Organometallics 1(12):1645

    CAS  Google Scholar 

  6. Schrock RR (2002) Chem Rev 102(1):145

    CAS  Google Scholar 

  7. Schrock RR, Czekelius C (2007) Adv Synth Catal 349(1–2):55

    CAS  Google Scholar 

  8. Furstner A, Davies PW (2005) Chem Commun (18): 2307

    Google Scholar 

  9. Beer S, Hrib CG, Jones PG, Brandhorst K, Grunenberg J, Tamm M (2007) Angew Chem Int Ed 46(46):8890

    CAS  Google Scholar 

  10. Laplaza CE, Odom AL, Davis WM, Cummins CC, Protasiewicz JD (1995) J Am Chem Soc 117(17):4999

    CAS  Google Scholar 

  11. Laplaza CE, Cummins CC (1995) Science 268(5212):861

    CAS  Google Scholar 

  12. Cummins C (1998) Chem Commun (17): 1777

    Google Scholar 

  13. Fürstner A, Mathes C, Lehmann CW (1999) J Am Chem Soc 121(40):9453

    Google Scholar 

  14. Zhang W, Kraft S, Moore JS (2003) Chem Commun (7): 832

    Google Scholar 

  15. Zhang W, Kraft S, Moore JS (2004) J Am Chem Soc 126(1):329

    CAS  Google Scholar 

  16. McCullough LG, Schrock RR (1984) J Am Chem Soc 106(14):4067

    CAS  Google Scholar 

  17. McCullough LG, Schrock RR, Dewan JC, Murdzek JC (1985) J Am Chem Soc 107(21):5987

    CAS  Google Scholar 

  18. Tsai Y-C, Diaconescu PL, Cummins CC (2000) Organometallics 19(25):5260

    CAS  Google Scholar 

  19. Heppekausen J, Stade R, Goddard R, Fürstner A (2010) J Am Chem Soc 132(32):11045

    CAS  Google Scholar 

  20. Vintonyak VV, Maier ME (2007) Org Lett 9(4):655

    CAS  Google Scholar 

  21. Vintonyak VV, Maier ME (2007) Angew Chem Int Ed 46(27):5209

    CAS  Google Scholar 

  22. Vintonyak VV, Calà M, Lay F, Kunze B, Sasse F, Maier ME (2008) Chem Eur J 14(12):3709

    CAS  Google Scholar 

  23. Fürstner A, Bindl M, Jean L (2007) Angew Chem Int Ed 46(48):9275

    Google Scholar 

  24. Bindl M, Jean L, Herrmann J, Müller R, Fürstner A (2009) Chem Eur J 15(45):12310

    CAS  Google Scholar 

  25. Micoine K, Fürstner A (2010) J Am Chem Soc 132(40):14064

    CAS  Google Scholar 

  26. Fürstner A, Grela K (2000) Angew Chem Int Ed 39(7):1234

    Google Scholar 

  27. Fürstner A, Grela K, Mathes C, Lehmann CW (2000) J Am Chem Soc 122(48):11799

    Google Scholar 

  28. Fürstner A, Larionov O, Flügge S (2007) Angew Chem Int Ed 46(29):5545

    Google Scholar 

  29. Fürstner A, Guth O, Rumbo A, Seidel G (1999) J Am Chem Soc 121(48):11108

    Google Scholar 

  30. Fürstner A, Langemann K (1997) Synthesis (07): 792

    Google Scholar 

  31. Yang Z, He Y, Vourloumis D, Vallberg H, Nicolaou KC (1997) Angew Chem Int Ed 36(1–2):166

    CAS  Google Scholar 

  32. Schinzer D, Limberg A, Bauer A, Böhm OM, Cordes M (1997) Angew Chem Int Ed 36(5):523

    CAS  Google Scholar 

  33. Meng D, Bertinato P, Balog A, Su D-S, Kamenecka T, Sorensen EJ, Danishefsky SJ (1997) J Am Chem Soc 119(42):10073

    CAS  Google Scholar 

  34. Furstner A, Mathes C, Grela K (2001) Chem Commun (12): 1057

    Google Scholar 

  35. Fürstner A, Turet L (2005) Angew Chem Int Ed 44(22):3462

    Google Scholar 

  36. Fürstner A, De Souza D, Turet L, Fenster MDB, Parra-Rapado L, Wirtz C, Mynott R, CW L m (2007) Chem Eur J 13(1):115

    Google Scholar 

  37. Fürstner A, Kirk D, Fenster MDB, Aïssa C, De Souza D, Nevado C, Tuttle T, Thiel W, Müller O (2007) Chem Eur J 13(1):135

    Google Scholar 

  38. Deiters A, Martin SF (2004) Chem Rev 104(5):2199

    CAS  Google Scholar 

  39. Deshmukh PH, Blechert S (2007) Dalton Trans (24): 2479

    Google Scholar 

  40. Snider BB, Song F (2001) Org Lett 3(12):1817

    CAS  Google Scholar 

  41. Fürstner A, Dierkes T, Thiel OR, Blanda G (2001) Chem Eur J 7(24):5286

    Google Scholar 

  42. Smith AB III, Zheng J (2002) Tetrahedron 58(32):6455

    CAS  Google Scholar 

  43. Wu Y, Liao X, Wang R, Xie X-S, De Brabander JK (2002) J Am Chem Soc 124(13):3245

    CAS  Google Scholar 

  44. Chen J, Forsyth CJ (2004) Angew Chem Int Ed 43(16):2148

    CAS  Google Scholar 

  45. Ghosh AK, Xu X (2004) Org Lett 6(12):2055

    CAS  Google Scholar 

  46. Ferrié L, Reymond S, Capdevielle P, Cossy J (2006) Org Lett 8(16):3441

    Google Scholar 

  47. Zhu G, Negishi E-i (2007) Org Lett 9(15):2771

    CAS  Google Scholar 

  48. Chandrasekhar S, Yaragorla SR, Sreelakshmi L, Reddy CR (2008) Tetrahedron 64(22):5174

    CAS  Google Scholar 

  49. Gaul C, Njardarson JT, Shan D, Dorn DC, Wu K-D, Tong WP, Huang X-Y, Moore MAS, Danishefsky SJ (2004) J Am Chem Soc 126(36):11326

    CAS  Google Scholar 

  50. Balog A, Meng D, Kamenecka T, Bertinato P, Su D-S, Sorensen EJ, Danishefsky SJ (1996) Angew Chem Int Ed 35(23–24):2801

    CAS  Google Scholar 

  51. Biswas K, Lin H, Njardarson JT, Chappell MD, Chou T-C, Guan Y, Tong WP, He L, Horwitz SB, Danishefsky SJ (2002) J Am Chem Soc 124(33):9825

    CAS  Google Scholar 

  52. Rivkin A, Yoshimura F, Gabarda AE, Chou T-C, Dong H, Tong WP, Danishefsky SJ (2003) J Am Chem Soc 125(10):2899

    CAS  Google Scholar 

  53. Funk RL, Abelman MM, Jellison KM (1989) Synlett (01): 36

    Google Scholar 

  54. Magriotis PA, Vourloumis D, Scott ME, Tarli A (1993) Tetrahedron Lett 34(13):2071

    CAS  Google Scholar 

  55. Liang L, Ramaseshan M, MaGee DI (1993) Tetrahedron 49(11):2159

    CAS  Google Scholar 

  56. Moslin RM, Jamison TF (2006) J Am Chem Soc 128(47):15106

    CAS  Google Scholar 

  57. Hyatt JA, Feldman PL, Clemens RJ (1984) J Org Chem 49(26):5105

    CAS  Google Scholar 

  58. Boeckman RK, Pruitt JR (1989) J Am Chem Soc 111(21):8286

    CAS  Google Scholar 

  59. Trost BM, Gunzner JL (2001) J Am Chem Soc 123(38):9449

    CAS  Google Scholar 

  60. Trost BM, Gunzner JL, Dirat O, Rhee YH (2002) J Am Chem Soc 124(35):10396

    CAS  Google Scholar 

  61. Marshall JA, Eidam PM (2007) Org Lett 10(1):93

    Google Scholar 

  62. Hoye TR, Danielson ME, May AE, Zhao H (2008) Angew Chem Int Ed 47(50):9743

    CAS  Google Scholar 

  63. Yadav JS, Haldar A, Maity T (2012) Eur J Org Chem: 2062

    Google Scholar 

  64. Xue H, Yang J, Gopal P (2011) Org Lett 13(20):5696

    CAS  Google Scholar 

  65. Williams DR, Myers BJ, Mi L (2000) Org Lett 2(7):945

    CAS  Google Scholar 

  66. Gebauer J, Blechert S (2006) J Org Chem 71(5):2021

    CAS  Google Scholar 

  67. Bhattacharjee A, De Brabander JK (2000) Tetrahedron Lett 41(42):8069

    CAS  Google Scholar 

  68. Hilli F, White JM, Rizzacasa MA (2002) Tetrahedron Lett 43(47):8507

    CAS  Google Scholar 

  69. Hilli F, White JM, Rizzacasa MA (2004) Org Lett 6(8):1289

    CAS  Google Scholar 

  70. Holloway GA, Hügel HM, Rizzacasa MA (2003) J Org Chem 68(6):2200

    CAS  Google Scholar 

  71. Saito S, Shiozawa M, Ito M, Yamamoto H (1998) J Am Chem Soc 120(4):813

    CAS  Google Scholar 

  72. Abramite JA, Sammakia T (2007) Org Lett 9(11):2103

    CAS  Google Scholar 

  73. Gazaille JA, Abramite JA, Sammakia T (2012) Org Lett 14(1):178

    CAS  Google Scholar 

  74. Bestmann HJ, Kellermann W, Pecher B (1993) Synthesis (01): 149

    Google Scholar 

  75. Blanchette MA, Choy W, Davis JT, Essenfeld AP, Masamune S, Roush WR, Sakai T (1984) Tetrahedron Lett 25(21):2183

    CAS  Google Scholar 

  76. Kanematsu M, Yoshida M, Shishido K (2011) Angew Chem Int Ed 50(11):2618

    CAS  Google Scholar 

  77. Jiang Y, Hong J, Burke SD (2004) Org Lett 6(9):1445

    CAS  Google Scholar 

  78. Kalivretenos A, Stille JK, Hegedus LS (1991) J Org Chem 56(8):2883

    CAS  Google Scholar 

  79. Piers E, Wong T (1993) J Org Chem 58(14):3609

    CAS  Google Scholar 

  80. Allred GD, Liebeskind LS (1996) J Am Chem Soc 118(11):2748

    CAS  Google Scholar 

  81. Paterson I, Lombart H-G, Allerton C (1999) Org Lett 1(1):19

    CAS  Google Scholar 

  82. Pilli RA, de Andrade CKZ, Souto CRO, de Meijere A (1998) J Org Chem 63(22):7811

    CAS  Google Scholar 

  83. Schreiber SL, Meyers HV (1988) J Am Chem Soc 110(15):5198

    CAS  Google Scholar 

  84. Venkatraman L, Salomon CE, Sherman DH, Fecik RA (2006) J Org Chem 71(26):9853

    CAS  Google Scholar 

  85. Oddon G, Uguen D (1998) Tetrahedron Lett 39(10):1157

    CAS  Google Scholar 

  86. Paek S-M, Seo S-Y, Kim S-H, Jung J-W, Lee Y-S, Jung J-K, Suh Y-G (2005) Org Lett 7(15):3159

    CAS  Google Scholar 

  87. Paek S-M, Suh Y-G (2011) Molecules 16(6):4850

    CAS  Google Scholar 

  88. Stang EM, Christina White M (2009) Nat Chem 1(7):547

    CAS  Google Scholar 

  89. Inanaga J, Hirata K, Saeki H, Katsuki T, Yamaguchi M (1979) Bull Chem Soc Jpn 52(7):1989

    CAS  Google Scholar 

  90. Evans DA, Connell BT (2003) J Am Chem Soc 125(36):10899

    CAS  Google Scholar 

  91. Spivey AC, Arseniyadis S (2004) Angew Chem Int Ed 43(41):5436

    CAS  Google Scholar 

  92. Storer RI, Takemoto T, Jackson PS, Brown DS, Baxendale IR, Ley SV (2004) Chem Eur J 10(10):2529

    CAS  Google Scholar 

  93. Evans DA, Black WC (1993) J Am Chem Soc 115(11):4497

    CAS  Google Scholar 

  94. Sarabia F, Chammaa S, López-Herrera FJ (2002) Tetrahedron Lett 43(16):2961

    CAS  Google Scholar 

  95. Fettes A, Carreira EM (2003) J Org Chem 68(24):9274

    CAS  Google Scholar 

  96. Barbazanges M, Meyer C, Cossy J (2008) J Org Lett 10(20):4489

    CAS  Google Scholar 

  97. McGowan MA, Stevenson CP, Schiffler MA, Jacobsen EN (2010) Angew Chem Int Ed 49(35):6147

    CAS  Google Scholar 

  98. Evans DA, Welch DS, Speed AWH, Moniz GA, Reichelt A, Ho S (2009) J Am Chem Soc 131(11):3840

    CAS  Google Scholar 

  99. Ghosh AK, Xu X, Kim J-H, Xu C-X (2008) Org Lett 10(5):1001

    CAS  Google Scholar 

  100. Corey EJ, Nicolaou KC (1974) J Am Chem Soc 96(17):5614

    CAS  Google Scholar 

  101. Endo T, Ikenaga S, Mukaiyama T (1970) Bull Chem Soc Jpn 43(8):2632

    CAS  Google Scholar 

  102. Mukaiyama T (1976) Angew Chem Int Ed Engl 15(2):94

    Google Scholar 

  103. Corey EJ, Clark DA (1979) Tetrahedron Lett 20(31):2875

    Google Scholar 

  104. Corey EJ, Brunelle DJ (1976) Tetrahedron Lett 17(38):3409

    Google Scholar 

  105. Schmidt U, Heermann D (1979) Angew Chem Int Ed Engl 18(4):308

    Google Scholar 

  106. Nimitz JS, Wollenberg RH (1978) Tetrahedron Lett 19(38):3523

    Google Scholar 

  107. Gerlach H, Thalmann A (1974) Helv Chim Acta 57(8):2661

    CAS  Google Scholar 

  108. Rastetter WH, Erickson TJ, Venuti MC (1980) J Org Chem 45(24):5011

    CAS  Google Scholar 

  109. Rastetter WH, Erickson TJ, Venuti MC (1981) J Org Chem 46(18):3579

    CAS  Google Scholar 

  110. Corey EJ, Bhattacharyya S (1977) Tetrahedron Lett 18(45):3919

    Google Scholar 

  111. Corey EJ, De B (1984) J Am Chem Soc 106(9):2735

    CAS  Google Scholar 

  112. Hillis LR, Ronald RC (1985) J Org Chem 50(4):470

    CAS  Google Scholar 

  113. Kusaka S-i, Dohi S, Doi T, Takahashi T (2003) Tetrahedron Lett 44(49):8857

    CAS  Google Scholar 

  114. Boden EP, Keck GE (1985) J Org Chem 50(13):2394

    CAS  Google Scholar 

  115. Kurihara T, Nakajima Y, Mitsunobu O (1976) Tetrahedron Lett 17(28):2455

    Google Scholar 

  116. Mitsunobu O (1981) Synthesis (01): 1

    Google Scholar 

  117. Mukaiyama T, Usui M, Saigo K (1976) Chem Lett 5(1):49

    Google Scholar 

  118. Narasaka K, Maruyama K, Mukaiyama T (1978) Chem Lett 7(8):885

    Google Scholar 

  119. Mukaiyama T (1979) Angew Chem Int Ed Engl 18(10):707

    Google Scholar 

  120. Schreiber SL, Kelly SE, Porco JA, Sammakia T, Suh EM (1988) J Am Chem Soc 110(18):6210

    CAS  Google Scholar 

  121. Armstrong A, Ley SV, Madin A, Mukherjee S (1990) Synlett 1990(06):328

    Google Scholar 

  122. Ley SV, Armstrong A, Diez-Martin D, Ford MJ, Grice P, Knight JG, Kolb HC, Madin A, Marby CA, Mukherjee S, Shaw AN, Slawin AMZ, Vile S, White AD, Williams DJ, Woods M (1991) J Chem Soc Perkin Trans 1(4):667

    Google Scholar 

  123. White JD, Bolton GL (1990) J Am Chem Soc 112(4):1626

    CAS  Google Scholar 

  124. White JD, Bolton GL, Dantanarayana AP, Fox CMJ, Hiner RN, Jackson RW, Sakuma K, Warrier US (1995) J Am Chem Soc 117(7):1908

    CAS  Google Scholar 

  125. Danishefsky SJ, Armistead DM, Wincott FE, Selnick HG, Hungate R (1987) J Am Chem Soc 109(26):8117

    CAS  Google Scholar 

  126. Danishefsky SJ, Armistead DM, Wincott FE, Selnick HG, Hungate R (1989) J Am Chem Soc 111(8):2967

    CAS  Google Scholar 

  127. Masamune S, Kamata S, Diakur J, Sugihara Y, Bates GS (1975) Can J Chem 53(23):3693

    CAS  Google Scholar 

  128. Diago-Meseguer J, Palomo-Coll AL, Fernández-Lizarbe JR, Zugaza-Bilbao A (1980) Synthesis (07): 547

    Google Scholar 

  129. Arrieta A, García T, Lago JM, Palomo C (1983) Synth Commun 13(6):471

    CAS  Google Scholar 

  130. Coste J, Frérot E, Jouin P, Castro B (1991) Tetrahedron Lett 32(17):1967

    CAS  Google Scholar 

  131. Frérot E, Coste J, Pantaloni A, Dufour M-N, Jouin P (1991) Tetrahedron 47(2):259

    Google Scholar 

  132. Coste J, Frerot E, Jouin P (1994) J Org Chem 59(9):2437

    CAS  Google Scholar 

  133. Kaiho T, Masamune S, Toyoda T (1982) J Org Chem 47(8):1612

    CAS  Google Scholar 

  134. Roush WR, Sciotti RJ (1998) J Am Chem Soc 120(30):7411

    CAS  Google Scholar 

  135. Hikota M, Tone H, Horita K, Yonemitsu O (1990) J Org Chem 55(1):7

    CAS  Google Scholar 

  136. Neises B, Steglich W (1978) Angew Chem Int Ed Engl 17(7):522

    Google Scholar 

  137. Colvin EW, Purcell TA, Raphael RA (1976) J Chem Soc Perkin Trans 1(16):1718

    Google Scholar 

  138. Taub D, Girotra NN, Hoffsommer RD, Kuo CH, Slates HL, Weber S, Wendler NL (1968) Tetrahedron 24(6):2443

    CAS  Google Scholar 

  139. Wood JL, Porco JA, Taunton J, Lee AY, Clardy J, Schreiber SL (1992) J Am Chem Soc 114(14):5898

    CAS  Google Scholar 

  140. Porco JA, Schoenen FJ, Stout TJ, Clardy J, Schreiber SL (1990) J Am Chem Soc 112(20):7410

    CAS  Google Scholar 

  141. Frank SA, Roush WR (2002) J Org Chem 67(12):4316

    CAS  Google Scholar 

  142. Keck GE, Sanchez C, Wager CA (2000) Tetrahedron Lett 41(45):8673

    CAS  Google Scholar 

  143. Ireland RE, Thaisrivongs S, Dussault PH (1988) J Am Chem Soc 110(17):5768

    CAS  Google Scholar 

  144. Feldman KS, Eastman KJ, Lessene G (2002) Org Lett 4(20):3525

    CAS  Google Scholar 

  145. Keck GE, Murry JA (1991) J Org Chem 56(23):6606

    CAS  Google Scholar 

  146. Trauner D, Schwarz JB, Danishefsky SJ (1999) Angew Chem Int Ed 38(23):3542

    CAS  Google Scholar 

  147. Jeong EJ, Kang EJ, Sung LT, Hong SK, Lee E (2002) J Am Chem Soc 124(49):14655

    CAS  Google Scholar 

  148. Lee E, Jeong EJ, Kang EJ, Sung LT, Hong SK (2001) J Am Chem Soc 123(41):10131

    CAS  Google Scholar 

  149. Evans DA, Ratz AM, Huff BE, Sheppard GS (1995) J Am Chem Soc 117(12):3448

    CAS  Google Scholar 

  150. Hatakeyama S, Osanai K, Numata H, Takano S (1989) Tetrahedron Lett 30(36):4845

    CAS  Google Scholar 

  151. Sellès P, Lett R (2002) Tetrahedron Lett 43(26):4627

    Google Scholar 

  152. Couladouros EA, Soufli IC, Moutsos VI, Chadha RK (1998) Chem Eur J 4(1):33

    CAS  Google Scholar 

  153. Li KW, Wu J, Xing W, Simon JA (1996) J Am Chem Soc 118(30):7237

    CAS  Google Scholar 

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Cordes, M., Kalesse, M. (2014). Synthesis of 12- to 16-Membered-Ring Lactones. In: Cossy, J. (eds) Synthesis of Saturated Oxygenated Heterocycles II. Topics in Heterocyclic Chemistry, vol 36. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-41470-1_3

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