Abstract
A series of 1′-homocarbanucleosides was prepared by coupling a purine or pyrimidine to, or constructing it on, a protected 1-methylcyclopenta[c ]pyrazole pseudosugar synthesized from (±)-(exo ,exo )-1-methyl-4,5,6,7-tetrahydro-4,7-methanoindazole-5,6-diol by oxidative cleavage of the starting glycol, reduction of the resulting dialdehyde with NaBH4 , and the protective monosilylation of the bis(hydroxymethyl) reduction product.
Key words
methanoindazoles - 1′(N )-homocarbanucleosides - nucleoside analogues - methylcyclopenta[c ]pyrazol - glycol cleavage - silyl ethers
References
1a Crimmins MT.
Tetrahedron
1998,
54:
9229
1b Agrofoglio L.
Challand SR.
Acyclic, Carbocyclic and l-Nucleosides
Kluwer Academic;
Dordrecht, The Netherlands:
1998.
p.1-320
1c Zhu XF.
Nucleosides, Nucleotides Nucleic Acids
2000,
19:
651
2a Madhavan GVB.
Martin JC.
J. Org. Chem.
1986,
51:
1287
2b Brown B.
Hegedus LS.
J. Org. Chem.
2000,
65:
1865
3a Franzyk H.
Rasmussen JH.
Mazzei RA.
Jensen SR.
Eur. J. Org. Chem.
1998,
2931
3b Lamberth C.
Org. Prep. Proced. Int.
2002,
34:
149
3c Saladino R.
Ciambecchini U.
Hanessian S.
Eur. J. Org. Chem.
2003,
4401
4 Thomas S.
McDowall JE.
Cheah V.
Bye A.
Segal MB.
The Entry of Abacavir into the Guinea-pig Brain: Comparison with Other Reverse Transcriptase Inhibitors
12th World AIDS Conference;
Geneva:
1998.
5 Blanco JM.
Caamaño O.
Fernández F.
Gómez G.
Nieto MI.
Balzarini J.
Padalko E.
De Clercq E.
Nucleosides Nucleotides
1997,
16:
159
6 Nieto MI.
Blanco JM.
Caamaño O.
Fernández F.
García-Mera X.
Balzarini J.
Padalko E.
Neyts J.
De Clercq E.
Nucleosides Nucleotides
1998,
17:
1255
7 Nieto MI.
Blanco JM.
Caamaño O.
Fernández F.
Gómez M.
Balzarini J.
De Clercq E.
Nucleosides, Nucleotides Nucleic Acids
2002,
21:
243
8 Fernández F.
García-Mera X.
Morales M.
Rodríguez-Borges JE.
De Clercq E.
Synthesis
2002,
1084
9 Yao S.-W.
López VHC.
Fernández F.
García-Mera X.
Morales M.
Rodríguez-Borges JE.
Cordeiro MNDS.
Bioorg. Med. Chem.
2003,
11:
4999
10 Fernández F.
García-Mera X.
Morales M.
Vilariño L.
Caamaño O.
De Clercq E.
Tetrahedron
2004,
60:
9245
11 López C.
Caamaño O.
Hergueta AR.
Fernández F.
García MD.
Tetrahedron Lett.
2002,
43:
5311
12 García MD.
Caamaño O.
Fernández F.
Figueira MJ.
Gómez G.
Synthesis
2003,
2138
13 Hergueta AR.
López C.
García-Mera X.
Fernández F.
Tetrahedron
2004,
60:
10343
14 García MD.
Caamaño O.
Fernández F.
López MC.
De Clercq E.
Synthesis
2005,
925
15 McDougal PG.
Rico JG.
Oh Y.-L.
Condon BD.
J. Org. Chem.
1986,
51:
3388
16 Mitsunobu O.
Synthesis
1981,
1
17 Dembinski R.
Eur. J. Org. Chem.
2004,
2763
18 Hossain N.
Blaton N.
Peeters O.
Rozenski J.
Herdewijn PA.
Tetrahedron
1996,
52:
5563
19a Gunaga P.
Baba M.
Jeong LS.
J. Org. Chem.
2004,
69:
3208
19b Russ P.
Schelling P.
Scapozza L.
Folkers G.
De Clercq E.
Marquez VE.
J. Med. Chem.
2003,
46:
5045
20 The crystallographic data of 9b and 17b have been deposited at the Cambridge Crystallographic Data Centre as supplementary publications numbers CCDC 269757 and 269758. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge, CB2 1EZ, UK.
21 Patil SD.
Koga M.
Schneller SW.
J. Med. Chem.
1992,
35:
2191
22 Fernández F.
García-Mera X.
Morales M.
Rodríguez-Borges JE.
Synthesis
2001,
239
