Synthetic Methodologies for C-Nucleosides

Qinpei Wu; Claire Simons

doi:10.1055/s-2004-829106

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Synthesis 2004(10): 1533-1553
DOI: 10.1055/s-2004-829106

REVIEW

Synthetic Methodologies for C-Nucleosides

Qinpei Wu*^a, Claire Simons*^b
^a School of Life Science and Technology, Beijing Institute of Technology, Beijing 100081, P. R. China
Fax: +86(10)68913293; e-Mail: qpwu@bit.edu.cn;
^b Welsh School of Pharmacy, Cardiff University, Cardiff CF10 3XF, UK
Fax: +44(29)20876307; e-Mail: simonsc@cardiff.ac.uk;

Further Information

Publication History

Received 26 February 2004
Publication Date:
23 June 2004 (online)

Abstract
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Abstract

The study and synthesis of C-nucleosides has been extensive owing to their biological activity and potential as drug candidates for antiviral and anticancer therapy. Numerous synthetic strategies have also been investigated in order to optimize yields and stereoselectivity in the glycosylation reaction. Here we review one class of synthetic methods, direct condensation of a pre-formed aglycon unit with an appropriate sugar component.

1 Introduction
2 Coupling of Ribofuranose Derivatives with Organometallic Reagents
3 Heck-Type Coupling Reaction
4 Coupling of Protected Ribofuranosyl Chlorides with Organometallic Reagents
5 Coupling of 1,4-Ribonolactone Derivatives with Organometallic Reagents
6 Coupling Reactions Mediated by Lewis Acids
7 Conclusions

Key words

C-nucleosides - organometallic reagents - Heck-type reaction - anticancer - antiviral

References

1 Simons C. Nucleoside Mimetics Their Chemistry and Biological Properties Gordon and Breach Science Publishers; Australia, Canada: 2001.

Google Scholar
2 Peasley K. Medical Hypotheses 2000, 55: 408

Crossref Google Scholar
3 Townsend LB. Chemistry of Nucleosides and Nucleotides Plenum Press; New York: 1994. p.421-535

Google Scholar
4 Miller PS. Antisense/Antigene Oligonucleotides, In Bioorganic Chemistry-Nucleic Acids Hecht SM. Oxford University Press; New York and Oxford: 1996. p.347-374

Google Scholar
5 Guntaka RV. Varma BR. Weber KT. Int. J. Biochem. Cell Biol. 2003, 35: 22

Crossref Google Scholar
6 Navarre J. Guianvarch D. Giorgio AF. Condom R. Benhida R. Tetrahedron Lett. 2003, 44: 2200

Google Scholar
7 Togo H. He W. Waki Y. Yokoyama M. Synlett 1998, 700

Article in Thieme Connect Google Scholar
8 Shaban AE. Nasr AZ. Adv. Heterocycl. Chem. 1998, 71: 164

Google Scholar
9 Shaban AE. Nasr AZ. Adv. Heterocycl. Chem. 1997, 68: 225

Google Scholar
10 Lerch U. Burdon MG. Moffatt JG. J. Org. Chem. 1968, 33: 140

Google Scholar
11 Brown DM. Burdon MG. J. Chem. Soc. 1968, 1051

Google Scholar
12 Kabat MM. Pankiewicz KW. Watanabe KA. J. Med. Chem. 1987, 30: 924

Crossref Google Scholar
13 Alderweireldt I. Vrijens EL. Esmans EL. Wotring LL. Townsend LB. De Clercq E. Nucleosides Nucleotides 1989, 8: 891

Google Scholar
14 Belmans M. Esmans E. Dommisse R. Lepoiver J. Alderweireldt F. Balzarini J. De Clercq E. Nucleosides Nucleotides 1985, 4: 523

Google Scholar
15 Belmans M. Vrijens I. Esmans E. Dommisse R. Lepoiver J. Alderweireldt F. Townsend L. Wotring J. Balzarini J. De Clercq E. Nucleosides Nucleotides 1986, 5: 441

Google Scholar
16 Yokoyama M. Toyoshima A. Akiba T. Togo H. Chem. Lett. 1994, 265

Google Scholar
17 Yokoyama M. Akiba T. Togo H. Synthesis 1995, 638

Article in Thieme Connect Google Scholar
18 Belmans M. Vrijens I. Esmans E. Dommisse R. Lepoiver J. Alderweireldt F. Townsend L. Wotring J. Balzarini J. De Clercq E. Nucleosides Nucleotides 1989, 8: 307

Google Scholar
19 Joose PE. Esmans EL. Dommisse RA. Lepiovre JA. Aldeweireldt FC. Nucleosides Nucleotides 1991, 10: 323

Google Scholar
20 Joose PE. Esmans EL. Dommisse RA. Van Dongen W. Lepiovre JA. Aldeweireldt FC. Balzarini J. De Clercq E. Nucleosides Nucleotides 1991, 10: 883

Google Scholar
21 Joose PE. Esmans EL. Dommisse RA. Brugh ADEW. Balzarini J. De Clercq E. Helv. Chim. Acta 1992, 75: 1613

Crossref Google Scholar
22 Solomon MS. Hopkins PB. Tetrahedron Lett. 1991, 32: 3297

Crossref Google Scholar
23 Brown DM. Ogden RC. J. Chem. Soc., Perkin Trans. 1 1981, 723

Crossref Google Scholar
24 Krohn K. Heins H. Wielckens K. J. Med. Chem. 1992, 35: 511

Crossref Google Scholar
25 Yokoyama M. Tanabe T. Togo H. Synthesis 1993, 517

Article in Thieme Connect Google Scholar
26 Harusawa S. Murai Y. Moriyama H. Imazu T. Ohishi H. Yoneda R. Kurihara T. J. Org. Chem. 1996, 61: 4405

Crossref PubMed Google Scholar
27 Yokoyama M. Tanabe T. Togo H. Chem. Lett. 1994, 265

Google Scholar
28 Chen JJ. Drach JC. Townsend LB. J. Org. Chem. 2003, 68: 4170

Crossref Google Scholar
29 Reese CB. Wu Q. Org. Biomol. Chem. 2003, 1: 3160

Crossref Google Scholar
30 Yokoyama M. Toyoshima H. Shimizu M. Togo H. J. Chem. Soc., Perkin Trans. 1 1997, 29

Crossref Google Scholar
32 Eaton MA. Millican AT. J. Chem. Soc., Perkin Trans. 1 1988, 545

Crossref Google Scholar
33 Obika S. Hari Y. Morio K. Imanishi T. Tetrahedron Lett. 2000, 41: 215

Crossref Google Scholar
34 Hari T. Obika S. Sakaki M. Morio K. Yamagata Y. Imanishi T. Tetrahedron 2003, 58: 3051

Google Scholar
35 Obika S. Hari Y. Sugimoto T. Sekiguchi M. Imanishi T. Tetrahedron Lett. 2000, 41: 8923

Crossref Google Scholar
36 Heck RF. Org. React. 1982, 27: 345

Google Scholar
37 Whitcombe N. Hii KK. Gibson SE. Tetrahedron 2001, 57: 7449

Crossref Google Scholar
38 Arai I. Daves GD. J. Am. Chem. Soc. 1978, 100: 287

Crossref Google Scholar
39 Cheng JY.-G. Hacksell U. Daves GD. J. Org. Chem. 1986, 51: 3093

Google Scholar
40 Hacksell U. Daves GD. J. Org. Chem. 1983, 48: 2870

Google Scholar
41 Hsieh HP. Mclaughlin LW. J. Org. Chem. 1995, 60: 5356

Crossref Google Scholar
42 Searls T. Chen DL. Lan T. Mclaughlin LW. Biochemistry 2000, 4375

Crossref Google Scholar
43 Zhang HC. Daves GD. J. Org. Chem. 1992, 57: 4690

Crossref Google Scholar
44 Zhang HC. Daves GD. J. Org. Chem. 1993, 58: 2557

Google Scholar
45 Farr RN. Kwok DI. Daves GD. J. Org. Chem. 1992, 57: 2093

Google Scholar
46 Chen DL. McLaughlin LW. J. Org. Chem. 2000, 65: 7468

Crossref Google Scholar
47 Liu H. Guo J. Maynard L. Saito D. Kool ET. J. Am. Chem. Soc. 2004, 126: 1102

Crossref Google Scholar
48 Liu H. Guo J. Lynch SR. Saito D. Maynard L. Kool ET. Science 2003, 302: 868

Crossref Google Scholar
49 Li J. Fan Y. Zhang Y. Marky LA. Gold B. J. Am. Chem. Soc. 2003, 125: 2084

Crossref PubMed Google Scholar
50 Li J. Shikiya R. Marky LA. Gold B. Biochemistry 2004, 43: 1440

Crossref Google Scholar
51 Coleman R. Madaras ML. J. Org. Chem. 1998, 63: 5700

Crossref Google Scholar
52 Miles RW. Tyler PC. Evans GB. Furneaux RH. Parkin DW. Schramm VL. Biochemistry 1999, 38: 13147

Crossref Google Scholar
53 Evans GB. Furneaux RH. Hutchison TL. Kezar HS. Morris PE. Schramm VL. Tyler PC. J. Org. Chem. 2001, 66: 5723

Crossref Google Scholar
54 Haberli A. Leumann CJ. Org. Lett. 2001, 3: 489

Crossref PubMed Google Scholar
55 Gudmundsson KS. Williams JD. Drach JC. Townsend LB. J. Med. Chem. 2003, 46: 1449

Crossref Google Scholar
56 Shapiro R. Chambers RW. J. Am. Chem. Soc. 1961, 83: 3920

Crossref Google Scholar
57 Mertes MP. Zielinski J. Pillar C. J. Med. Chem. 1967, 320

Crossref Google Scholar
58 Chaudhuri NC. Kool ET. Tetrahedron Lett. 1995, 36: 1795

Crossref Google Scholar
59 Chen DW. Beuscher AE. Stevens RC. Wirsching P. Lerner RA. Janda KD. J. Org. Chem. 2001, 66: 1725

Crossref Google Scholar
60 Ren R. Chaudhuri NC. Paris PL. Rumney PS. Kool ET. J. Am. Chem. Soc. 1996, 118: 7671

Crossref Google Scholar
61 Chaudhuri NC. Ren RX.-F. Kool ET. Synlett 1997, 341

Article in Thieme Connect Google Scholar
62 Pirrung MC. Zhao X. Harris SV. J. Org. Chem. 2001, 66: 2067

Crossref Google Scholar
63 Strassler C. Davis NE. Kool ET. Helv. Chem. Acta 1999, 82: 2160

Crossref Google Scholar
64 Beuck C. Singh I. Bhattacharya A. Hecker W. Parmar VS. Seitz O. Weinhold E. Angew. Chem. Int. Ed. 2003, 42: 3958

Crossref Google Scholar
65x Wang ZX. Duan W. Wiebe LI. Balzarini J. Clercq ED. Knaus EE. Nucleosides Nucleotides 2001, 20: 11

Google Scholar
65 Piccirilli JA. Krauch T. Macpherson LJ. Benner SA. Helv. Chim. Acta 1991, 397

Crossref Google Scholar
66 Liu W. Walker JA. Chen JJ. Wise DS. Townsend LB. Tetrahedron Lett. 1996, 37: 5325

Crossref Google Scholar
67 Liu W. Wise DS. Townsend LB. J. Org. Chem. 2001, 66: 4783

Crossref Google Scholar
68 Joose PE. Esmans EL. De Clercq E. Nucleosides Nucleotides 1991, 10: 853

Google Scholar
69 Hildbran S. Blaser A. Parel SP. Leumann CJ. J. Am. Chem. Soc. 1997, 119: 5499

Crossref Google Scholar
71x Brotschi C. Häberli A. Leumann C. Angew. Chem. Int. Ed. 2001, 40: 3012

Crossref Google Scholar
70 Tanaka K. Shionoya M. J. Org. Chem. 1999, 64: 5002

Crossref Google Scholar
71 Wichai V. Woski SA. Bioorg. Med. Chem. Lett. 1998, 3465

Crossref Google Scholar
72 Wichai U. Woski SA. Org. Lett. 1999, 1173

Crossref Google Scholar
73 Matulic-Adamic J. Beigelman L. Tetrahedron Lett. 1997, 38: 204

Google Scholar
74 Matulic-Adamic J. Beigelman L. Tetrahedron Lett. 1997, 38: 1669

Crossref Google Scholar
75 Gudmundsson KS. Drach JC. Townsend LB. Tetrahedron Lett. 1996, 37: 2365

Crossref Google Scholar
76 Gudmundsson KS. Drach JC. Townsend LB. J. Org. Chem. 1997, 62: 3453

Crossref Google Scholar
77 Asbun W. Binkley SB. J. Org. Chem. 1968, 31: 140

Google Scholar
78 Pankiewicz KW. Sochacka E. Kabat MM. Ciszewski LA. Watanabe KA. J. Org. Chem. 1988, 53: 3473

Google Scholar
79 Pankiewicz KW. Kabat MM. Sochacka E. Ciszewski L. Zeidler J. Watanabe AK. Nucleosides Nucleotides 1988, 7: 389

Google Scholar
80 Ogara H. Takashi H. J. Org. Chem. 1974, 37: 1374

Google Scholar
81 Kabat MM. Pankiewicz KW. Sochacka E. Watanabe KA. Chem. Pharm. Bull. Jpn. 1988, 36: 634

Google Scholar
83 Sollogoub M. Fox KR. Powers VE. Brown T. Tetrahedron Lett. 2002, 43: 3121

Crossref Google Scholar
84 Kabat MM. Pankiewiez KW. Watanable KA. J. Med. Chem. 1987, 924

Crossref Google Scholar
85 Ogura H. Takahashi H. J. Org. Chem. 1974, 39: 1374

Google Scholar
86 Pankiewicz KW. Kabat MM. Sochacka E. Ciszewski L. Zeidler J. Watanabe AK. Nucleosides Nucleotides 1988, 8: 589

Google Scholar
87 Verberckmoes FC. Esmans EL. Balzarini J. De Clerq E. Nucleosides Nucleotides 1991, 10: 1771

Google Scholar
88 Alderweireldt F. Vrijens I. Esmans E. Wortring J. Townsend L. Balzarini J. De Clercq E. Nucleosides Nucleotides 1988, 7: 891

Google Scholar
89 Verberckmoes FC. Esmans EL. Balzarini J. De Clerq E. Nucleosides Nucleotides 1994, 13: 511

Google Scholar
90 Guianvarc’h D. Benhida R. Fourrey JL. Tetrahedron Lett. 2001, 42: 647

Crossref Google Scholar
91 Guianvarc’h D. Fourrey JL. Huu Dau M. Guérineau V. Benhida R. J. Org. Chem. 2002, 67: 3724

Crossref Google Scholar
93 Hanessian S. Machaalani R. Tetrahedron Lett. 2003, 44: 8321

Crossref Google Scholar
94 Navarre J.-M. Guianvarc’h D. Farese-Di Giorgio A. Condon R. Benhida R. Tetrahedron Lett. 2003, 44: 2199

Crossref Google Scholar
95 Yokoyama M. Ikenogami T. Togo H. J. Chem. Soc., Perkin Trans. 1 2000, 2067

Crossref Google Scholar
96 Momotake A. Togo H. Yokoyama M. J. Chem. Soc., Perkin Trans. 1 1999, 1193

Crossref Google Scholar
97 Diese B. Dupuis J. Angew. Chem., Int. Ed. Engl. 1983, 22: 622

Google Scholar
98 Dupuis J. Diese B. Ruegge D. Fischer H. Korth HG. Sustmann R. J. Am. Chem. Soc. 1985, 107: 4332

Crossref Google Scholar
99 Girgis NS. Michael MA. Smee DF. Alaghamandan HA. Robins RK. Cottam HB. J. Med. Chem. 1990, 33: 2750

Crossref Google Scholar
100 Farr RN. Kwok DI. Daves GD. J. Org. Chem. 1992, 2093

Google Scholar
101 Inoue T. Kuwujima I. J. Chem. Soc., Chem. Commun. 1980, 251

Crossref Google Scholar
102 Rao P. Rao KVB. Otter BA. Kelein RS. Ren WY. Tetrahedron Lett. 1988, 29: 3537

Crossref Google Scholar
103 Patil SA. Otter BA. Klein RS. J. Heterocycl. Chem. 1993, 509

Google Scholar
104 Mumper MW. Aurenge C. Hosmane RS. Bioorg. Med. Chem. Lett. 1993, 3: 2847

Crossref Google Scholar
105 Stewart AO. Williams RM. J. Am. Chem. Soc. 1985, 107: 4289

Crossref Google Scholar
106 Farkas J. Flegelova Z. Sorm F. Tetrahedron Lett. 1972, 2279

Crossref Google Scholar
107 He W. Togo H. Yokoyama M. Tetrahedron Lett. 1997, 5541

Crossref Google Scholar
108 Barton DHR. Ramesh M. J. Am. Chem. Soc. 1990, 112: 891

Crossref Google Scholar
109 Mukaiyama T. Hirano N. Nishida M. Uchiro H. Chem. Lett. 1997, 389

Crossref Google Scholar

31

Reese, C. B.; Wu, Q.; Capaldi, D. unpublished results.