Snyder, S. A.: 2016 Science of Synthesis, 2015/4a: Applications of Domino Transformations in Organic Synthesis 1 DOI: 10.1055/sos-SD-219-00067
Applications of Domino Transformations in Organic Synthesis 1

1.3.1 Enyne-Metathesis-Based Domino Reactions in Natural Product Synthesis

Weitere Informationen

Buch

Herausgeber: Snyder, S. A.

Autoren: Adu-Ampratwum, D.; Anderson, E.; Armbrust, K. W.; Devery, J.; Douglas, J.; Doyle, M. P.; Engle, K. M.; Forsyth, C. J.; Gille, F.; Halkina, T.; Hu, X.; Jamison, T.; Kelley, E. H.; Kirschning, A.; Lee, D.; Maimone, T.; Merino, E.; Nevado Blazquez, C.; O'Connor, M. J.; Ohshima, T.; Parker, K.; Renata, H.; Salvador, A.; Schaumann, E.; Shenvi, R.; Shi, L.-L.; Sittihan, S.; Snyder, S. A.; Stephenson, C. R. J.; Tang, M.; Truong, P.; Tu, Y.-Q.; Wan, K.; Wang, S.-H.; Wolling, M.; Xu, X.; Yang, Z.

Titel: Applications of Domino Transformations in Organic Synthesis 1

Print ISBN: 9783131731319; Online ISBN: 9783132402522; Buch-DOI: 10.1055/b-003-128286

Fachgebiete: Organische Chemie;Chemische Reaktionen, Katalyse;Organometallchemie;Chemische Labormethoden, Stöchiometrie

Science of Synthesis Reference Libraries



Übergeordnete Publikation

Titel: Science of Synthesis

DOI: 10.1055/b-00000101

Reihenherausgeber: Carreira, E. M.; Decicco, C. P.; Fürstner, A.; Koch, G.; Molander, G.; Schaumann, E.; Shibasaki, M.; Thomas, E. J.; Trost, B. M.

Typ: Mehrbändiges Werk

 


Abstract

Enyne-metathesis-based domino processes are highlighted in the context of natural product synthesis; these include domino double ring-closing metathesis, enyne metathesis/metallotropic [1,3]-shifts, enyne metathesis/Diels–Alder reaction, and other variations of their domino combinations. Issues regarding selectivity and mechanism are also discussed.

 
  • 1 Tietze LF, Beifuss U. Angew. Chem. 1993; 105: 137 Angew. Chem. Int. Ed. Engl. 1993; 32: 131
  • 2 Tietze LF. Chem. Ind. (London) 1995; 453
  • 3 Waldmann H, Organic Synthesis Highlights II. Waldmann H. VCH Weinheim, Germany 1995; p 193
  • 4 Hall N. Science (Washington, D. C.) 1994; 266: 32
  • 5 Domino Reactions in Organic Synthesis. Tietze LF, Brasche G, Gericke KM. Wiley-VCH; Weinheim, Germany 2006
  • 6 Wasilke J.-C, Obrey SJ, Baker RT, Bazan GC. Chem. Rev. 2005; 105: 1001
  • 7 Parsons PJ, Penkett CS, Shell AJ. Chem. Rev. 1996; 96: 195
  • 8 Tietze LF, Rackelmann N. Pure Appl. Chem. 2004; 76: 1976
  • 9 Trost BM. Angew. Chem. 1995; 107: 285 Angew. Chem. Int. Ed. Engl. 1995; 34: 259
  • 10 Sheldon RA. Pure Appl. Chem. 2000; 72: 1233
  • 11 Trost BM. Acc. Chem. Res. 2002; 35: 695
  • 12 Wender PA, Verma VA, Paxton TJ, Pillow TH. Acc. Chem. Res. 2008; 41: 40
  • 13 Sivavec TM, Katz TJ. Tetrahedron Lett. 1985; 26: 2159
  • 14 Katz TJ, Sivavec TM. J. Am. Chem. Soc. 1985; 107: 737
  • 15 Korkowski PF, Hoye TR, Rydberg DB. J. Am. Chem. Soc. 1988; 110: 2676
  • 16 Hoye TR, Rehberg GM. Organometallics 1989; 8: 2070
  • 17 Hoye TR, Rehberg GM. J. Am. Chem. Soc. 1990; 112: 2841
  • 18 Watanuki S, Ochifuji N, Mori M. Organometallics 1994; 13: 4129
  • 19 Watanuki S, Mori M. Organometallics 1995; 14: 5054
  • 20 Watanuki S, Ochifuji N, Mori M. Organometallics 1995; 14: 5062
  • 21 Kinoshita A, Mori M. Synlett 1994; 1020
  • 22 Kim S.-H, Bowden N, Grubbs RH. J. Am. Chem. Soc. 1994; 116: 10801
  • 23 Mori M, In Handbook of Metathesis. Grubbs RH. Wiley-VCH; Weinheim, Germany 2003. Vol. 2 p  176.
  • 24 Schrock RR, Murdzek JS, Bazan GC, Robbins J, DiMare M, OʼRegan M. J. Am. Chem. Soc. 1990; 112: 3875
  • 25 Lee Y.-J, Schrock RR, Hoveyda AH. J. Am. Chem. Soc. 2009; 131: 10652
  • 26 Zhao Y, Hoveyda AH, Schrock RR. Org. Lett. 2011; 13: 784
  • 27 Casey CP, Kraft S, Powell DR. J. Am. Chem. Soc. 2002; 124: 2584
  • 28 Hansen EC, Lee D. J. Am. Chem. Soc. 2004; 126: 15074
  • 29 Lippstreu JJ, Straub BF. J. Am. Chem. Soc. 2005; 127: 7444
  • 30 Galan BR, Giessert AJ, Keister JB, Diver ST. J. Am. Chem. Soc. 2005; 127: 5762
  • 31 Giessert AJ, Diver ST. Org. Lett. 2005; 7: 351
  • 32 Lloyd-Jones GC, Margue RG, de Vries JG. Angew. Chem. 2005; 117: 7608 Angew. Chem. Int. Ed. 2005; 44: 7442
  • 33 Dieltiens N, Moonen K, Stevens C. V. Chem.–Eur. J. 2007; 13: 203
  • 34 Marshall JE, Keister JB, Diver ST. Organometallics 2011; 30: 1319
  • 35 Ulman M, Grubbs RH. Organometallics 1998; 17: 2484
  • 36 Hoye TR, Donaldson SM, Vos TJ. Org. Lett. 1999; 1: 277
  • 37 Schramm MP, Reddy DS, Kozmin SA. Angew. Chem. 2001; 113: 4404 Angew. Chem. Int. Ed. 2001; 40: 4274
  • 38 Clavier H, Correa A, Escudero-Adán EC, Benet-Buchholz J, Cavallo L, Nolan SP. Chem.–Eur. J. 2009; 15: 10244
  • 39 Kitamura T, Sato Y, Mori M. Chem. Commun. (Cambridge) 2001; 1258
  • 40 Kitamura T, Sato Y, Mori M. Adv. Synth. Catal. 2002; 344: 678
  • 41 Nuñez-Zarur F, Solans-Monfort X, Rodríguez-Santiago L, Pleixats R, Sodupe M. Chem.–Eur. J. 2011; 17: 7506
  • 42 Sohn J.-H, Kim K. H, Lee H.-Y, No Z. S, Ihee H. J. Am. Chem. Soc. 2008; 130: 16506
  • 43 Miyanohana Y, Inoue H, Chatani N. J. Org. Chem. 2004; 69: 8541
  • 44 Bajracharya GB, Nakamura I, Yamamoto Y. J. Org. Chem. 2005; 70: 892
  • 45 Nieto-Oberhuber C, Muñoz MP, Buñuel E, Nevado C, Cárdenas DJ, Echavarren AM. Angew. Chem. 2004; 116: 2456 Angew. Chem. Int. Ed. 2004; 43: 2402
  • 46 Nieto-Oberhuber C, Muñoz MP, López S, Jiménez-Núñez E, Nevado C, Herrero-Gómez E, Raducan M, Echavarren AM. Chem.–Eur. J. 2006; 12: 1677
  • 47 Ferrer C, Raducan M, Nevado C, Claverie CK, Echavarren AM. Tetrahedron 2007; 63: 6306
  • 48 Lee D, Kim M. Org. Biomol. Chem. 2007; 5: 3418
  • 49 Skell PS, Klebe J. J. Am. Chem. Soc. 1960; 82: 247
  • 50 Bergman RG, Rajadhyaksha VJ. J. Am. Chem. Soc. 1970; 92: 2163
  • 51 Franck-Neumann M, Geoffroy P, Lohmann JJ. Tetrahedron Lett. 1983; 24: 1775
  • 52 Franck-Neumann M, Geoffroy P. Tetrahedron Lett. 1983; 24: 1779
  • 53 Padwa A, Gareau Y, Xu SL. Tetrahedron Lett. 1991; 32: 983
  • 54 Noro M, Masuda T, Ichimura AS, Koga N, Iwamura H. J. Am. Chem. Soc. 1994; 116: 6179
  • 55 Hauptmann H. Tetrahedron 1976; 32: 1293
  • 56 Hori Y, Noda K, Kobayashi S, Taniguchi H. Tetrahedron Lett. 1969; 3563
  • 57 Okada S, Peng S, Spevak W, Charych D. Acc. Chem. Res. 1998; 31: 229
  • 58 Song J, Cheng Q, Zhu S, Stevens RC. Biomed. Microdevices 2002; 4: 213
  • 59 Koyanagi T, Muratsubaki M, Hosoi Y, Shibata T, Tsutsui K, Wada Y, Furukawa Y. Chem. Lett. 2006; 35: 20
  • 60 Kim M, Miller RL, Lee D. J. Am. Chem. Soc. 2005; 127: 12818
  • 61 Kim M, Park S, Maifeld SV, Lee D. J. Am. Chem. Soc. 2004; 126: 10242
  • 62 Park S, Kim M, Lee D. J. Am. Chem. Soc. 2005; 127: 9410
  • 63 Kim M, Lee D. Org. Lett. 2005; 7: 1865
  • 64 Hansen EC, Lee D. J. Am. Chem. Soc. 2003; 125: 9582
  • 65 Miller RL, Maifeld SV, Lee D. Org. Lett. 2004; 6: 2773
  • 66 Lee H.-Y, Kim B. G, Snapper ML. Org. Lett. 2003; 5: 1855
  • 67 Giessert AJ, Diver ST. J. Org. Chem. 2005; 70: 1046
  • 68 Watanabe K, Minato H, Murata M, Oishi T. Heterocycles 2007; 72: 207
  • 69 Wang K.-P, Cho EJ, Yun SY, Rhee JY, Lee D. Tetrahedron 2013; 69: 9105
  • 70 Yun SY, Kim M, Lee D, Wink DJ. J. Am. Chem. Soc. 2009; 131: 24
  • 71 Laplaza CE, Odom AL, Davis WM, Cummins CC, Protasiewicz JD. J. Am. Chem. Soc. 1995; 117: 4999
  • 72 Cummins CC. Chem. Commun. (Cambridge) 1998; 1777
  • 73 Fürstner A, Flügge S, Larionov O, Takahashi Y, Kubota T, Kobayashi J. Chem.–Eur. J. 2009; 15: 4011
  • 74 Volchkov I, Lee D. J. Am. Chem. Soc. 2013; 135: 5324
  • 75 Ko HM, Lee CW, Kwon HK, Chung HS, Choi SY, Chung YK, Lee E. Angew. Chem. 2009; 121: 2400 Angew. Chem. Int. Ed. 2009; 48: 2364
  • 76 Debleds O, Campagne J.-M. J. Am. Chem. Soc. 2008; 130: 1562
  • 77 Graham TJA, Gray EE, Burgess JM, Goess BC. J. Org. Chem. 2010; 75: 226
  • 78 Reddy DS, Kozmin SA. J. Org. Chem. 2004; 69: 4860
  • 79 Hoye TR, Zhao H. Org. Lett. 1999; 1: 1123
  • 80 Hoye TR, Promo MA. Tetrahedron Lett. 1999; 40: 1429
  • 81 Imahori T, Ojima H, Yoshimura Y, Takahata H. Chem.–Eur. J. 2008; 14: 10762
  • 82 Imahori T, Ojima H, Tateyama H, Mihara Y, Takahata H. Tetrahedron Lett. 2008; 49: 265
  • 83 Zhu X, Sheth KA, Li S, Chang H.-H, Fan J.-Q. Angew. Chem. 2005; 117: 7616 Angew. Chem. Int. Ed. 2005; 44: 7450
  • 84 MuniRaju C, Rao JP, Rao B. V. Tetrahedron: Asymmetry 2012; 23: 86
  • 85 Krishna PR, Reddy PS. Synlett 2009; 209
  • 86 Aggarwal VK, Astle CJ, Rogers-Evans M. Org. Lett. 2004; 6: 1469
  • 87 Brenneman JB, Martin SF. Org. Lett. 2004; 6: 1329
  • 88 Mori M, Tomita T, Kita Y, Kitamura T. Tetrahedron Lett. 2004; 45: 4397
  • 89 Tomita T, Kita Y, Kitamura T, Sato Y, Mori M. Tetrahedron 2006; 62: 10518
  • 90 Boyer F.-D, Hanna I, Ricard L. Org. Lett. 2004; 6: 1817
  • 91 Boyer F.-D, Hanna I. Eur. J. Org. Chem. 2006; 471
  • 92 Mandal M, Yun H, Dudley GB, Lin S, Tan DS, Danishefsky SJ. J. Org. Chem. 2005; 70: 10619
  • 93 Lee J, Parker KA. Org. Lett. 2012; 14: 2682
  • 94 Molawi K, Delpont N, Echavarren AM. Angew. Chem. 2010; 122: 3595 Angew. Chem. Int. Ed. 2010; 49: 3517
  • 95 Movassaghi M, Piizzi G, Siegel DS, Piersanti G. Angew. Chem. 2006; 118: 5991 Angew. Chem. Int. Ed. 2006; 45: 5859
  • 96 Siegel DS, Piizzi G, Piersanti G, Movassaghi M. J. Org. Chem. 2009; 74: 9292
  • 97 Schubert M, Metz P. Angew. Chem. 2011; 123: 3011 Angew. Chem. Int. Ed. 2011; 50: 2954
  • 98 Kim YJ, Lee D. Org. Lett. 2006; 8: 5219
  • 99 Mukherjee S, Lee D. Org. Lett. 2009; 11: 2916
  • 100 Dineen TA, Roush WR. Org. Lett. 2004; 6: 2043
  • 101 Ramharter J, Weinstabl H, Mulzer J. J. Am. Chem. Soc. 2010; 132: 14338
  • 102 Niethe A, Fischer D, Blechert S. J. Org. Chem. 2008; 73: 3088
  • 103 Honda T, Namiki H, Kaneda K, Mizutani H. Org. Lett. 2004; 6: 87
  • 104 Shimizu K, Takimoto M, Mori M. Org. Lett. 2003; 5: 2323
  • 105 Fukumoto H, Esumi T, Ishihara J, Hatakeyama S. Tetrahedron Lett. 2003; 44: 8047
  • 106 Wei H, Qiao C, Liu G, Yang Z, Li C.-C. Angew. Chem. 2013; 125: 648 Angew. Chem. Int. Ed. 2013; 52: 620
  • 107 Hansen EC, Lee D. Acc. Chem. Res. 2006; 39: 509
  • 108 Wallace DJ. Angew. Chem. 2005; 117: 1946 Angew. Chem. Int. Ed. 2005; 44: 1912
  • 109 Kummer DA, Brenneman JB, Martin SF. Tetrahedron 2006; 62: 11437
  • 110 Evans MA, Morken JP. Org. Lett. 2005; 7: 3371
  • 111 Li J, Lee D. Chem.–Asian J. 2010; 5: 1298
  • 112 Lei X, Johnson RP, Porco Jr JA. Angew. Chem. 2003; 115: 4043 Angew. Chem. Int. Ed. 2003; 42: 3913
  • 113 Moses JE, Commeiras L, Baldwin JE, Adlington RM. Org. Lett. 2003; 5: 2987
  • 114 Layton ME, Morales CA, Shair MD. J. Am. Chem. Soc. 2002; 124: 773
  • 115 Morales CA, Layton ME, Shair MD. Proc. Natl. Acad. Sci. U. S. A. 2004; 101: 12036
  • 116 Kim CH, An HJ, Shin WK, Yu W, Woo SK, Jung SK, Lee E. Chem.–Asian J. 2008; 3: 1523
  • 117 Kim CH, An HJ, Shin WK, Yu W, Woo SK, Jung SK, Lee E. Angew. Chem. 2006; 118: 8187 Angew. Chem. Int. Ed. 2006; 45: 8019
  • 118 Li J, Park S, Miller RL, Lee D. Org. Lett. 2009; 11: 571
  • 119 Cho EJ, Lee D. Org. Lett. 2008; 10: 257
  • 120 Kim H, Lee H, Lee D, Kim S, Kim D. J. Am. Chem. Soc. 2007; 129: 2269
  • 121 Ramharter J, Mulzer J. Org. Lett. 2009; 11: 1151
  • 122 Kaliappan KP, Subrahmanyam AV. Org. Lett. 2007; 9: 1121
  • 123 Kaliappan KP, Ravikumar V. Synlett 2007; 977
  • 124 Kaliappan KP, Ravikumar V. J. Org. Chem. 2007; 72: 6116
  • 125 Kurhade SE, Sanchawala AI, Ravikumar V, Bhuniya D, Reddy DS. Org. Lett. 2011; 13: 3690
  • 126 Trost BM, Doherty GA. J. Am. Chem. Soc. 2000; 122: 3801
  • 127 Fürstner A, Weintritt H. J. Am. Chem. Soc. 1998; 120: 2817
  • 128 Fürstner A, Szillat H, Gabor B, Mynott R. J. Am. Chem. Soc. 1998; 120: 8305