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
Pennella F, Banks RL, Bailey GC (1968) Chem Commun (23): 1548
Mortreux A, Blanchard M (1974) J Chem Soc Chem Commun 19:786
Fürstner A, Stelzer F, Rumbo A, Krause H (2002) Chem Eur J 8(8):1856
Wengrovius JH, Sancho J, Schrock RR (1981) J Am Chem Soc 103(13):3932
Schrock RR, Clark DN, Sancho J, Wengrovius JH, Rocklage SM, Pedersen SF (1982) Organometallics 1(12):1645
Schrock RR (2002) Chem Rev 102(1):145
Schrock RR, Czekelius C (2007) Adv Synth Catal 349(1–2):55
Furstner A, Davies PW (2005) Chem Commun (18): 2307
Beer S, Hrib CG, Jones PG, Brandhorst K, Grunenberg J, Tamm M (2007) Angew Chem Int Ed 46(46):8890
Laplaza CE, Odom AL, Davis WM, Cummins CC, Protasiewicz JD (1995) J Am Chem Soc 117(17):4999
Laplaza CE, Cummins CC (1995) Science 268(5212):861
Cummins C (1998) Chem Commun (17): 1777
Fürstner A, Mathes C, Lehmann CW (1999) J Am Chem Soc 121(40):9453
Zhang W, Kraft S, Moore JS (2003) Chem Commun (7): 832
Zhang W, Kraft S, Moore JS (2004) J Am Chem Soc 126(1):329
McCullough LG, Schrock RR (1984) J Am Chem Soc 106(14):4067
McCullough LG, Schrock RR, Dewan JC, Murdzek JC (1985) J Am Chem Soc 107(21):5987
Tsai Y-C, Diaconescu PL, Cummins CC (2000) Organometallics 19(25):5260
Heppekausen J, Stade R, Goddard R, Fürstner A (2010) J Am Chem Soc 132(32):11045
Vintonyak VV, Maier ME (2007) Org Lett 9(4):655
Vintonyak VV, Maier ME (2007) Angew Chem Int Ed 46(27):5209
Vintonyak VV, Calà M, Lay F, Kunze B, Sasse F, Maier ME (2008) Chem Eur J 14(12):3709
Fürstner A, Bindl M, Jean L (2007) Angew Chem Int Ed 46(48):9275
Bindl M, Jean L, Herrmann J, Müller R, Fürstner A (2009) Chem Eur J 15(45):12310
Micoine K, Fürstner A (2010) J Am Chem Soc 132(40):14064
Fürstner A, Grela K (2000) Angew Chem Int Ed 39(7):1234
Fürstner A, Grela K, Mathes C, Lehmann CW (2000) J Am Chem Soc 122(48):11799
Fürstner A, Larionov O, Flügge S (2007) Angew Chem Int Ed 46(29):5545
Fürstner A, Guth O, Rumbo A, Seidel G (1999) J Am Chem Soc 121(48):11108
Fürstner A, Langemann K (1997) Synthesis (07): 792
Yang Z, He Y, Vourloumis D, Vallberg H, Nicolaou KC (1997) Angew Chem Int Ed 36(1–2):166
Schinzer D, Limberg A, Bauer A, Böhm OM, Cordes M (1997) Angew Chem Int Ed 36(5):523
Meng D, Bertinato P, Balog A, Su D-S, Kamenecka T, Sorensen EJ, Danishefsky SJ (1997) J Am Chem Soc 119(42):10073
Furstner A, Mathes C, Grela K (2001) Chem Commun (12): 1057
Fürstner A, Turet L (2005) Angew Chem Int Ed 44(22):3462
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
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
Deiters A, Martin SF (2004) Chem Rev 104(5):2199
Deshmukh PH, Blechert S (2007) Dalton Trans (24): 2479
Snider BB, Song F (2001) Org Lett 3(12):1817
Fürstner A, Dierkes T, Thiel OR, Blanda G (2001) Chem Eur J 7(24):5286
Smith AB III, Zheng J (2002) Tetrahedron 58(32):6455
Wu Y, Liao X, Wang R, Xie X-S, De Brabander JK (2002) J Am Chem Soc 124(13):3245
Chen J, Forsyth CJ (2004) Angew Chem Int Ed 43(16):2148
Ghosh AK, Xu X (2004) Org Lett 6(12):2055
Ferrié L, Reymond S, Capdevielle P, Cossy J (2006) Org Lett 8(16):3441
Zhu G, Negishi E-i (2007) Org Lett 9(15):2771
Chandrasekhar S, Yaragorla SR, Sreelakshmi L, Reddy CR (2008) Tetrahedron 64(22):5174
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
Balog A, Meng D, Kamenecka T, Bertinato P, Su D-S, Sorensen EJ, Danishefsky SJ (1996) Angew Chem Int Ed 35(23–24):2801
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
Rivkin A, Yoshimura F, Gabarda AE, Chou T-C, Dong H, Tong WP, Danishefsky SJ (2003) J Am Chem Soc 125(10):2899
Funk RL, Abelman MM, Jellison KM (1989) Synlett (01): 36
Magriotis PA, Vourloumis D, Scott ME, Tarli A (1993) Tetrahedron Lett 34(13):2071
Liang L, Ramaseshan M, MaGee DI (1993) Tetrahedron 49(11):2159
Moslin RM, Jamison TF (2006) J Am Chem Soc 128(47):15106
Hyatt JA, Feldman PL, Clemens RJ (1984) J Org Chem 49(26):5105
Boeckman RK, Pruitt JR (1989) J Am Chem Soc 111(21):8286
Trost BM, Gunzner JL (2001) J Am Chem Soc 123(38):9449
Trost BM, Gunzner JL, Dirat O, Rhee YH (2002) J Am Chem Soc 124(35):10396
Marshall JA, Eidam PM (2007) Org Lett 10(1):93
Hoye TR, Danielson ME, May AE, Zhao H (2008) Angew Chem Int Ed 47(50):9743
Yadav JS, Haldar A, Maity T (2012) Eur J Org Chem: 2062
Xue H, Yang J, Gopal P (2011) Org Lett 13(20):5696
Williams DR, Myers BJ, Mi L (2000) Org Lett 2(7):945
Gebauer J, Blechert S (2006) J Org Chem 71(5):2021
Bhattacharjee A, De Brabander JK (2000) Tetrahedron Lett 41(42):8069
Hilli F, White JM, Rizzacasa MA (2002) Tetrahedron Lett 43(47):8507
Hilli F, White JM, Rizzacasa MA (2004) Org Lett 6(8):1289
Holloway GA, Hügel HM, Rizzacasa MA (2003) J Org Chem 68(6):2200
Saito S, Shiozawa M, Ito M, Yamamoto H (1998) J Am Chem Soc 120(4):813
Abramite JA, Sammakia T (2007) Org Lett 9(11):2103
Gazaille JA, Abramite JA, Sammakia T (2012) Org Lett 14(1):178
Bestmann HJ, Kellermann W, Pecher B (1993) Synthesis (01): 149
Blanchette MA, Choy W, Davis JT, Essenfeld AP, Masamune S, Roush WR, Sakai T (1984) Tetrahedron Lett 25(21):2183
Kanematsu M, Yoshida M, Shishido K (2011) Angew Chem Int Ed 50(11):2618
Jiang Y, Hong J, Burke SD (2004) Org Lett 6(9):1445
Kalivretenos A, Stille JK, Hegedus LS (1991) J Org Chem 56(8):2883
Piers E, Wong T (1993) J Org Chem 58(14):3609
Allred GD, Liebeskind LS (1996) J Am Chem Soc 118(11):2748
Paterson I, Lombart H-G, Allerton C (1999) Org Lett 1(1):19
Pilli RA, de Andrade CKZ, Souto CRO, de Meijere A (1998) J Org Chem 63(22):7811
Schreiber SL, Meyers HV (1988) J Am Chem Soc 110(15):5198
Venkatraman L, Salomon CE, Sherman DH, Fecik RA (2006) J Org Chem 71(26):9853
Oddon G, Uguen D (1998) Tetrahedron Lett 39(10):1157
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
Paek S-M, Suh Y-G (2011) Molecules 16(6):4850
Stang EM, Christina White M (2009) Nat Chem 1(7):547
Inanaga J, Hirata K, Saeki H, Katsuki T, Yamaguchi M (1979) Bull Chem Soc Jpn 52(7):1989
Evans DA, Connell BT (2003) J Am Chem Soc 125(36):10899
Spivey AC, Arseniyadis S (2004) Angew Chem Int Ed 43(41):5436
Storer RI, Takemoto T, Jackson PS, Brown DS, Baxendale IR, Ley SV (2004) Chem Eur J 10(10):2529
Evans DA, Black WC (1993) J Am Chem Soc 115(11):4497
Sarabia F, Chammaa S, López-Herrera FJ (2002) Tetrahedron Lett 43(16):2961
Fettes A, Carreira EM (2003) J Org Chem 68(24):9274
Barbazanges M, Meyer C, Cossy J (2008) J Org Lett 10(20):4489
McGowan MA, Stevenson CP, Schiffler MA, Jacobsen EN (2010) Angew Chem Int Ed 49(35):6147
Evans DA, Welch DS, Speed AWH, Moniz GA, Reichelt A, Ho S (2009) J Am Chem Soc 131(11):3840
Ghosh AK, Xu X, Kim J-H, Xu C-X (2008) Org Lett 10(5):1001
Corey EJ, Nicolaou KC (1974) J Am Chem Soc 96(17):5614
Endo T, Ikenaga S, Mukaiyama T (1970) Bull Chem Soc Jpn 43(8):2632
Mukaiyama T (1976) Angew Chem Int Ed Engl 15(2):94
Corey EJ, Clark DA (1979) Tetrahedron Lett 20(31):2875
Corey EJ, Brunelle DJ (1976) Tetrahedron Lett 17(38):3409
Schmidt U, Heermann D (1979) Angew Chem Int Ed Engl 18(4):308
Nimitz JS, Wollenberg RH (1978) Tetrahedron Lett 19(38):3523
Gerlach H, Thalmann A (1974) Helv Chim Acta 57(8):2661
Rastetter WH, Erickson TJ, Venuti MC (1980) J Org Chem 45(24):5011
Rastetter WH, Erickson TJ, Venuti MC (1981) J Org Chem 46(18):3579
Corey EJ, Bhattacharyya S (1977) Tetrahedron Lett 18(45):3919
Corey EJ, De B (1984) J Am Chem Soc 106(9):2735
Hillis LR, Ronald RC (1985) J Org Chem 50(4):470
Kusaka S-i, Dohi S, Doi T, Takahashi T (2003) Tetrahedron Lett 44(49):8857
Boden EP, Keck GE (1985) J Org Chem 50(13):2394
Kurihara T, Nakajima Y, Mitsunobu O (1976) Tetrahedron Lett 17(28):2455
Mitsunobu O (1981) Synthesis (01): 1
Mukaiyama T, Usui M, Saigo K (1976) Chem Lett 5(1):49
Narasaka K, Maruyama K, Mukaiyama T (1978) Chem Lett 7(8):885
Mukaiyama T (1979) Angew Chem Int Ed Engl 18(10):707
Schreiber SL, Kelly SE, Porco JA, Sammakia T, Suh EM (1988) J Am Chem Soc 110(18):6210
Armstrong A, Ley SV, Madin A, Mukherjee S (1990) Synlett 1990(06):328
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
White JD, Bolton GL (1990) J Am Chem Soc 112(4):1626
White JD, Bolton GL, Dantanarayana AP, Fox CMJ, Hiner RN, Jackson RW, Sakuma K, Warrier US (1995) J Am Chem Soc 117(7):1908
Danishefsky SJ, Armistead DM, Wincott FE, Selnick HG, Hungate R (1987) J Am Chem Soc 109(26):8117
Danishefsky SJ, Armistead DM, Wincott FE, Selnick HG, Hungate R (1989) J Am Chem Soc 111(8):2967
Masamune S, Kamata S, Diakur J, Sugihara Y, Bates GS (1975) Can J Chem 53(23):3693
Diago-Meseguer J, Palomo-Coll AL, Fernández-Lizarbe JR, Zugaza-Bilbao A (1980) Synthesis (07): 547
Arrieta A, GarcÃa T, Lago JM, Palomo C (1983) Synth Commun 13(6):471
Coste J, Frérot E, Jouin P, Castro B (1991) Tetrahedron Lett 32(17):1967
Frérot E, Coste J, Pantaloni A, Dufour M-N, Jouin P (1991) Tetrahedron 47(2):259
Coste J, Frerot E, Jouin P (1994) J Org Chem 59(9):2437
Kaiho T, Masamune S, Toyoda T (1982) J Org Chem 47(8):1612
Roush WR, Sciotti RJ (1998) J Am Chem Soc 120(30):7411
Hikota M, Tone H, Horita K, Yonemitsu O (1990) J Org Chem 55(1):7
Neises B, Steglich W (1978) Angew Chem Int Ed Engl 17(7):522
Colvin EW, Purcell TA, Raphael RA (1976) J Chem Soc Perkin Trans 1(16):1718
Taub D, Girotra NN, Hoffsommer RD, Kuo CH, Slates HL, Weber S, Wendler NL (1968) Tetrahedron 24(6):2443
Wood JL, Porco JA, Taunton J, Lee AY, Clardy J, Schreiber SL (1992) J Am Chem Soc 114(14):5898
Porco JA, Schoenen FJ, Stout TJ, Clardy J, Schreiber SL (1990) J Am Chem Soc 112(20):7410
Frank SA, Roush WR (2002) J Org Chem 67(12):4316
Keck GE, Sanchez C, Wager CA (2000) Tetrahedron Lett 41(45):8673
Ireland RE, Thaisrivongs S, Dussault PH (1988) J Am Chem Soc 110(17):5768
Feldman KS, Eastman KJ, Lessene G (2002) Org Lett 4(20):3525
Keck GE, Murry JA (1991) J Org Chem 56(23):6606
Trauner D, Schwarz JB, Danishefsky SJ (1999) Angew Chem Int Ed 38(23):3542
Jeong EJ, Kang EJ, Sung LT, Hong SK, Lee E (2002) J Am Chem Soc 124(49):14655
Lee E, Jeong EJ, Kang EJ, Sung LT, Hong SK (2001) J Am Chem Soc 123(41):10131
Evans DA, Ratz AM, Huff BE, Sheppard GS (1995) J Am Chem Soc 117(12):3448
Hatakeyama S, Osanai K, Numata H, Takano S (1989) Tetrahedron Lett 30(36):4845
Sellès P, Lett R (2002) Tetrahedron Lett 43(26):4627
Couladouros EA, Soufli IC, Moutsos VI, Chadha RK (1998) Chem Eur J 4(1):33
Li KW, Wu J, Xing W, Simon JA (1996) J Am Chem Soc 118(30):7237
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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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