Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2014; 46(09): 1129-1142
DOI: 10.1055/s-0033-1340952
DOI: 10.1055/s-0033-1340952
review
Tetraethyl Vinylidenebisphosphonate: A Versatile Synthon for the Preparation of Bisphosphonates
Further Information
Publication History
Received: 17 October 2013
Accepted after revision: 04 December 2013
Publication Date:
19 March 2014 (online)
Abstract
Tetraethyl vinylidenebisphosphonate is a versatile synthetic intermediate that allows access to a variety of highly functionalized compounds bearing the bisphosphonic moiety. As an electron-deficient alkene, this compound is able to undergo conjugate addition with a variety of reagents including strong nucleophiles, such as organometallic reagents and enolates, as well as very mild nucleophiles, such as amines, mercaptans and alcohols. The title compound also possesses the ability to behave as a dipolarophile or dienophile in 1,3-dipolar cycloadditions or Diels–Alder reactions, giving rise to five- or six-membered rings containing the bisphosphonic unit. In summary, tetraethyl vinylidenebisphosphonate is a very useful synthon to have at hand for straightforward syntheses of bisphosphonate derivatives of diverse structures. This bisphosphonate moiety has proven to be very important to impart important pharmacological action.
1 Introduction
2 General Reactivity
3 Michael Addition Reactions
3.1 Reaction with Organometallic Reagents
3.2 Reaction with Mercaptans and Amines
3.3 Reaction with Phosphorus-Containing Nucleophiles
3.4 Epoxidation, Loss of a Phosphonate Unit and Rearrangement Reactions
3.5 Michael Reactions with Enolates
4. Cycloaddition Reactions
4.1 Diels–Alder Reactions
4.2 1,3-Dipolar Cycloadditions
4.2.1 Reaction with Diazo Compounds
4.2.2 Reaction with Nitrones
4.2.3 Reaction with Nitrile Oxides
4.2.4 Grigg Azomethine Ylide Cyclizations
4.2.5 Reaction with Azides
5 Concluding Remarks
-
References
- 1 Roelofs AJ, Thompson K, Ebetino FH, Rogers MJ, Coxon FP. Curr. Pharm. Des. 2010; 16: 2950
- 2 Fleisch H, Russell RG. G, Straumann F. Nature 1966; 212: 901
- 3 Fleisch H, Russell RG. G, Francis MD. Science 1969; 165: 1262
- 4 Francis MD, Russell RG. G, Fleisch H. Science 1969; 165: 1264
- 5 Degenhardt CR, Burdsall DC. J. Org. Chem. 1986; 51: 3488
- 6 Page PC. B, Moore JP. G, Mansfield I, McKenzie MJ, Bowler WB, Gallagher JA. Tetrahedron 2001; 57: 1837
- 7 Lolli ML, Lazzarato L, Di Stilo A, Fruttero R, Gasco A. J. Organomet. Chem. 2002; 650: 77
- 8 Sturtz G, Guervenou J. Synthesis 1991; 661
- 9 Ford-Moore AH, Williams JH. J. Chem. Soc. 1947; 1465
- 10 Inoue S, Okauchi T, Minami T. Synthesis 2003; 1971
- 11 Okauchi T, Yano T, Fukamachi T, Ichikawa J, Minami T. Tetrahedron Lett. 1999; 40: 5337
- 12 Lehnert W. Tetrahedron 1974; 30: 301
- 13 Ding H, Xu G, Wang J, Zhang Y, Wu X, Xie Y. Heteroat. Chem. 2004; 15: 549
- 14 Russell RG. G. Bone 2011; 49: 2
- 15 Reszka AA, Rodan GA. Mini-Rev. Med. Chem. 2004; 4: 711
- 16 Rogers MJ. Bone 1999; 25: 97
- 17 Reszka AA, Rodan GA. Curr. Osteoporos. Rep. 2003; 1: 45
- 18 Miller K, Erez R, Segal E, Shabat D, Satchi-Fainaro R. Angew. Chem. Int. Ed. 2009; 48: 2949
- 19 Clézardin P, Massaia M. Curr. Pharm. Des. 2010; 16: 3007
- 20 Coleman RE. Br. J. Cancer 2008; 98: 1736
- 21 Zhang Y, Cao R, Yin F, Hudock MP, Guo R.-T, Krysiak K, Mukherjee S, Gao Y.-G, Robinson H, Song Y, No JH, Bergan K, Leon A, Cass L, Goddard A, Chang T.-K, Lin F.-Y, Van Beek E, Papapoulos S, Wang AH.-J, Kubo T, Ochi M, Mukkamala D, Oldfield E. J. Am. Chem. Soc. 2009; 131: 5153
- 22 Reddy R, Dietrich E, Lafontaine Y, Houghton TJ, Belanger O, Dubois A, Arhin FF, Sarmiento I, Fadhil I, Laquerre K, Ostiguy V, Lehoux D, Moeck G, Parr Jr TR, Rafai Far A. ChemMedChem 2008; 3: 1863
- 23 Roth AG, Drescher D, Yang Y, Yang Y, Redmer S, Uhlig S, Arenz C. Angew. Chem. Int. Ed. 2009; 48: 7560
- 24 Sanders JM, Ghosh S, Chan JM. W, Meints G, Wang H, Raker AM, Song Y, Colantino A, Burzynska A, Kafarski P, Morita CT, Oldfield E. J. Med. Chem. 2004; 47: 375
- 25 Ghosh S, Chan JM. W, Lea CR, Meints GA, Lewis JC, Tovian ZS, Flessner RM, Loftus TC, Bruchhaus I, Kendrick H, Croft SL, Kemp RG, Kobayashi S, Nozaki T, Oldfield E. J. Med. Chem. 2004; 47: 175
- 26 Martin MB, Grimley JS, Lewis JC, Heath III HT, Bailey BN, Kendrick H, Yardley V, Caldera A, Lira R, Urbina JA, Moreno SN, Docampo R, Croft SL, Oldfield E. J. Med. Chem. 2001; 44: 909
- 27 Yardley V, Khan AA, Martin MB, Slifer TR, Araujo FG, Moreno SN. J, Docampo R, Croft SL, Oldfield E. Antimicrob. Agents Chemother. 2002; 46: 929
- 28 Martin MB, Sanders JM, Kendrick H, de Luca-Fradley K, Lewis JC, Grimley JS, Van Brussel EM, Olsen JR, Meints GA, Burzynska A, Kafarski P, Croft SL, Oldfield E. J. Med. Chem. 2002; 45: 2904
- 29 Rodriguez JB, Szajnman SH. Expert Opin. Ther. Patents 2012; 22: 311
- 30 García Liñares G, Ravaschino EL, Rodriguez JB. Curr. Med. Chem. 2006; 13: 335
- 31 Docampo R, Moreno SN. J. Curr. Pharm. Des. 2008; 14: 882
- 32 Oldfield E. Acc. Chem. Res. 2010; 43: 1216
- 33 Kieczykowski GR, Jobson RB, Melillo DG, Reinhold DF, Grenda VJ, Shinkai I. J. Org. Chem. 1995; 60: 8310
- 34 Widler LK, Jaeggi A, Glatt M, Müller K, Bachman R, Bisping M, Born A-R, Cortesi R, Guiglia G, Jeker H, Klein R, Ramseier U, Schmid J, Schreiber G, Seltenmeyer Y, Green JR. J. Med. Chem. 2002; 45: 3721
- 35 Olive G, Le Moigne F, Mercier A, Tordo P. Synth. Commun. 2000; 34: 617
- 36 Griffiths DV, Hughes JM, Brown JW, Caesar JC, Swetnam SP, Cumming SA, Kelly JD. Tetrahedron 1997; 53: 17815
- 37 Takeuchi M, Sakamoto S, Yoshida M, Abe T, Isomura Y. Chem. Pharm. Bull. 1993; 41: 688
- 38 Szajnman SH, Montalvetti A, Wang Y, Docampo R, Rodríguez JB. Bioorg. Med. Chem. Lett. 2003; 13: 3231
- 39 Szajnman SH, Liñares GG, Moro P, Rodriguez JB. Eur. J. Org. Chem. 2005; 3687
- 40 Szajnman SH, Rosso VS, Malayil L, Smith A, Moreno SN. J, Docampo R, Rodriguez JB. Org. Biomol. Chem. 2012; 10: 1424
- 41 Skarpos H, Osipov SN, Vorob’eva DV, Odinets IL, Lork E, Röschenthaler G.-V. Org. Biomol. Chem. 2007; 5: 2361
- 42a Rosso VS, Szajnman SH, Malayil L, Galizzi M, Moreno SN. J, Docampo R, Rodriguez JB. Bioorg. Med. Chem. 2011; 19: 2211
- 42b Szajnman SH, García Liñares GE, Li Z.-H, Galizzi M, Jiang C, Bontempi E, Ferella M, Moreno SN. J, Docampo R, Rodriguez JB. Bioorg. Med. Chem. 2008; 16: 3283
- 42c Houghton TJ, Tanaka KS. E, Kang T, Dietrich E, Lafontaine Y, Delorme D, Ferreira SS, Viens F, Arhin FF, Sarmiento I, Lehoux D, Fadhil I, Laquerre K, Liu J, Ostiguy V, Poirier H, Moeck G, Parr Jr TR, Far AR. J. Med. Chem. 2008; 51: 6955
- 43 Simoni D, Gebbia N, Invidiata FP, Eleopra M, Marchetti P, Rondanin R, Baruchello R, Provera S, Marchioro C, Tolomeo M, Marinelli L, Limongelli V, Novellino E, Kwaasi A, Dunford J, Buccheri S, Caccamo N, Dieli F. J. Med. Chem. 2008; 51: 6800
- 44 Delain-Bioton L, Turner A, Lejeune N, Villemin D, Hix GB, Jaffrès P.-A. Tetrahedron 2005; 61: 6602
- 45 Recher M, Barboza AP, Li Z.-H, Galizzi M, Ferrer-Casal M, Szajnman SH, Docampo R, Moreno SN. J, Rodriguez JB. Eur. J. Med. Chem. 2013; 60: 431
- 46a Page PC. B, McKenzie MJ, Gallagher JA. J. Org. Chem. 2001; 66: 3704
- 46b Couthon-Gourvès H, Simon G, Haelters J.-P, Corbel B. Synthesis 2006; 81
- 46c Schlachter ST, Galinet LA, Shields SK, Aspar DG, Dunn CJ, Staite ND, Nugent RA. Bioorg. Med. Chem. Lett. 1998; 8: 1093
- 47 Ruzziconi R, Ricci G, Gioiello A, Couthon-Gourvès H, Gourvès J.-P. J. Org. Chem. 2003; 68: 736
- 48 Nugent RA, Murphy M, Schlachter ST, Dunn CJ, Smith RJ, Staite ND, Galinet LA, Shields SK, Aspar DG, Richard KA, Rohlofft NA. J. Med. Chem. 1993; 36: 134
- 49 Bortolini O, Mulani I, De Nino A, Maiuolo L, Nardi M, Russo B, Avnet S. Tetrahedron 2011; 67: 5635
- 50 Ye Y, Xu G.-Y, Zheng Y, Liu L.-Z. Heteroat. Chem. 2003; 14: 309
- 51 Ferrer-Casal M, Barboza AP, Szajnman SH, Rodriguez JB. Synthesis 2013; 45: 2397
- 52 Almstead NG, Dansereau SM, Francis MD, Snider CM, Ebetino FH. Phosphorus, Sulfur Silicon Relat. Elem. 1999; 144–146: 325
- 53 Cahiez G, Alexakis A, Normant JF. Tetrahedron Lett. 1978; 19: 3013
- 54 Hutchinson DW, Thornton DM. J. Organomet. Chem. 1988; 346: 341
- 55 Nicotra F, Panza L, Russo G. J. Chem. Soc., Chem. Commun. 1984; 5
- 56 Herczegh P, Buxton TB, McPherson III JC, Kovács-Kulyassa Á, Brewer PD, Sztaricskai F, Stroebel GG, Plowman KM, Farcasiu D, Hartmann JF. J. Med. Chem. 2002; 45: 2338
- 57 Madesclaire M. Tetrahedron 1986; 42: 5459
- 58 Oldfield E, Song Y, Zhang Y, Sanders JM. WO2007/109585A2, 2007
- 59 Mikołajczyk M, Zatorski A. Synthesis 1973; 669
- 60 Leonard NJ, Johnson CR. J. Org. Chem. 1962; 27: 282
- 61 Mikołajczyk M, Grzejszczak S, Zatorski A. J. Org. Chem. 1975; 40: 1979
- 62 Drabowicz J, Mikołajczyk M. Synthesis 1978; 758
- 63 Barthélémy P, Maurizis JC, Lacombe JM, Pucci B. Bioorg. Med. Chem. Lett. 1998; 8: 1559
- 64 Aversa MC, Barattucci A, Bonaccorsi P, Giannetto P. J. Org. Chem. 2005; 70: 1986
- 65 Aversa MC, Barattucci A, Bonaccorsi P, Marino-Merlo F, Mastino A, Sciortino MT. Bioorg. Med. Chem. 2009; 17: 1456
- 66 Aversa MC, Barattucci A, Bilardo MC, Bonaccorsi P, Giannetto P, Rollin P, Tatibouët A. J. Org. Chem. 2005; 70: 7389
- 67 Horhant D, Le Lamer A.-C, Boustie J, Uriac P, Gouault N. Tetrahedron Lett. 2007; 48: 6031
- 68 Borbás A, Herczegh P. Carbohydr. Res. 2011; 346: 1628
- 69 Brajeswar P, Korytnyk V. Carbohydr. Res. 1984; 126: 27
- 70 Burgos-Lepley CE, Mizsak SA, Nugent RA, Johnson RA. J. Org. Chem. 1993; 58: 4159
- 71 Duncan GD, Li Z.-M, Khare AB, McKenna CE. J. Org. Chem. 1995; 60: 7080
- 72 Fotsing MC. D, Coville N, Mbianda XY. Heteroat. Chem. 2013; 24: 234
- 73 Cristau H.-J, Mbianda XY, Geze A, Beziat Y, Gasc M.-B. J. Organomet. Chem. 1998; 571: 189
- 74 Lecerclé D, Sawicki M, Taran F. Org. Lett. 2006; 8: 4283
- 75 Prashad M. Tetrahedron Lett. 1993; 34: 1585
- 76 Holstein SA, Cermark DM, Wiemer DF, Lewis K, Hohl RJ. Bioorg. Med. Chem. 1998; 6: 687
- 77 Minowa N, Hirayama M, Fukatsu S. Tetrahedron Lett. 1984; 25: 1147
- 78 Ruiz M, Ojea V, Shapiro G, Weber H.-P. Tetrahedron Lett. 1994; 35: 4551
- 79 Enders D, Wahl H, Papadopoulos K. Tetrahedron 1997; 53: 12961
- 80 Sulzer-Mossé S, Alexakis A. Chem. Commun. 2007; 3123
- 81 Sulzer-Mossé S, Tissot M, Alexakis A. Org. Lett. 2007; 9: 3749
- 82 Hayashi Y, Gotoh H, Hayashi T, Shoji M. Angew. Chem. Int. Ed. 2005; 44: 4212
- 83 Fránzen L, Marigo M, Fielenbach D, Wabnitz TC, Kjærsgaard A, Jørgensen KA. J. Am. Chem. Soc. 2005; 127: 18296
- 84 Marigo M, Bertelsen S, Landa A, Jørgensen KA. J. Am. Chem. Soc. 2006; 128: 5475
- 85 Sulzer-Mossé S, Alexakis A, Mareda J, Bollot G, Bernardinelli G, Filinchuk Y. Chem. Eur. J. 2009; 15: 3204
- 86 Saito S, Nakadai H, Yamamoto H. Synlett 2001; 1245
- 87 Mukherjee S, Yang JW, Hoffmann S, List B. Chem. Rev. 2007; 107: 5471
- 88 Barros MT, Faísca Phillips AM. Eur. J. Org.Chem. 2008; 2525
- 89 Barros MT, Faísca Phillips AM. Org. Biomol. Chem. 2012; 10: 404
- 90 Chen Z, Morimoto H, Matsunaga S, Shibasaki M. J. Am. Chem. Soc. 2008; 130: 2170
- 91 Kato Y, Chen Z, Matsunaga S, Shibasaki M. Synlett 2009; 1635
- 92 Capuzzi M, Perdicchia D, Jørgensen KA. Chem. Eur. J. 2008; 14: 128
- 93 Stanley LM, Sibi MP. Chem. Rev. 2008; 108: 2887
- 94 Xue Z.-Y, Liu T.-L, Lu Z, Tao H.-Y, Wang C.-J. Chem. Commun. 2010; 46: 1727
- 95 Xue Z.-Y, Li Q.-H, Tao H.-Y, Wang C.-J. J. Am. Chem. Soc. 2011; 133: 11757
- 96 Carruthers W. Cycloaddition Reactions in Organic Synthesis . Pergamon; Oxford: 1991: 269-331
- 97 Kosolapoff GM. J. Am. Chem. Soc. 1948; 70: 1971
- 98 Daniewski WM, Griffin CE. J. Org. Chem. 1966; 31: 3236
- 99a Defacqz N, Touillaux R, Marchand-Brynaert J. J. Chem. Res., Miniprint 1998; 2273
- 99b Defacqz N, Touillaux R, Tinant B, Declercq J.-P, Peeters D, Marchand-Brynaert J. J. Chem. Soc., Perkin Trans. 2 1997; 1965
- 100 McClure CK, Hansen KB. Tetrahedron Lett. 1996; 37: 2149
- 101a Barembom M, Fones WS. J. Am. Chem. Soc. 1949; 71: 1629
- 101b Newman MS, Beal P. J. Am. Chem. Soc. 1949; 71: 1506
- 102 Regitz M, Menz F, Rueter J. Tetrahedron Lett. 1967; 8: 739
- 103 Carruthers W. Cycloaddition Reactions in Organic Synthesis . Pergamon; Oxford: 1991: 298-313
- 104 Nguyen TB, Beauseigneur A, Martel A, Dhal R, Laurent M, Dujardin G. J. Org. Chem. 2010; 75: 611
- 105 Houk KN. Acc. Chem. Res. 1975; 8: 361
- 106 Huigsen R. Angew. Chem., Int. Ed. Engl. 1963; 2: 565
- 107 Fleming I. Molecular Orbitals and Organic Chemical Reactions . John Wiley & Sons; New York: 2009: 242-252
- 108 Mendelsohn BA, Lee S, Kim S, Teyssier F, Aulakh VS, Ciufolini MA. Org. Lett. 2009; 11: 1539
- 109a Grigg R, Kemp J, Sheldrick G, Trotter J. J. Chem. Soc., Chem. Commun. 1978; 109
- 109b Joucla M, Hamelin J. Tetrahedron Lett. 1978; 19: 2885
- 110a Garner P, Kaniskan HÜ. Tetrahedron Lett. 2005; 46: 5181
- 110b Garner P, Kaniskan HÜ. J. Org. Chem. 2005; 70: 10868
- 111 Gothelf KV, Jørgensen KA. Chem. Rev. 1998; 98: 863
- 112 Sha C.-K, Mohanakrishnan AK. Azides. In The Chemistry of Heterocyclic Compounds: Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products. Vol. 59. Padwa A, Pearson WH. John Wiley & Sons; New York: 2002: 623-679
- 113 Chakrasali RT, Ila H, Junjappa H. Synthesis 1988; 453
- 114 Jiang Q, Yang L, Hai L, Wu Y. Lett. Org. Chem. 2008; 5: 229
- 115 Chen X, Li X, Yuan J, Qu L, Wang S, Shi H, Tang Y, Duan L. Tetrahedron 2013; 69: 4047
- 116 Zhou X, Hartman SV, Born EJ, Smits JP, Holstein SA, Wiemer DF. Bioorg. Med. Chem. Lett. 2013; 23: 764