RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
PDF herunterladen
Synthesis 2018; 50(11): 2266-2280
DOI: 10.1055/s-0037-1609493
DOI: 10.1055/s-0037-1609493
paper
Synthesis of Enantiomerically Pure 1′,2′-cis-dideoxy, -dideoxydidehydro, -ribo and -deoxy Carbocyclic Nucleoside Analogues
Authors
The authors are grateful to Universität Hamburg for financial support.
Weitere Informationen
Publikationsverlauf
Received: 25. Januar 2018
Accepted after revision: 06. März 2018
Publikationsdatum:
12. April 2018 (online)
Abstract
We describe a short and stereospecific synthesis of different series of 1′,2′-cis-disubstituted carbocyclic nucleoside analogues. All-natural nucleobases or their precursors are coupled in a microwave-assisted Mitsunobu-type reaction with enantiomerically pure (1R,2S)-2-(benzyloxymethyl)cyclopent-3-enol. By modifying the cyclopentene scaffold, our synthetic strategy gives access to a series of 1′,2′-cis-disubstituted carbocyclic nucleoside analogues of the dideoxy (dd), dideoxydidehydro (d4) or the ribo series. The ribo series is synthesized in a more convenient way compared to a previous route. The deoxy series of 1′,2′-cis-disubstituted carbocyclic nucleoside analogues is prepared following an earlier reported approach. This synthesis involves the microwave-assisted coupling of (1R,2S,3S)-3-(benzyloxy)-2-[(benzyloxy)methyl]cyclopentan-1-ol with the appropriate nucleobases.
Key words
carbocycles - Mitsunobu coupling - 1′,2′-cis-substitution - microwave reaction - nucleosidesSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1609493.
- Supporting Information (PDF)
-
References
- 1a De Clercq E. Nat. Rev. Drug Discovery 2002; 1: 13
- 1b Jordheim LP. Durantel D. Zoulim F. Dumontet C. Nat. Rev. Drug Discovery 2013; 12: 447
- 2 Matthée G. Wright AD. König GM. Planta Med. 1999; 65: 493
- 3 Welzel TM. Nelson DR. Morelli G. Di Bisceglie A. Reddy RK. Kuo A. Lim JK. Darling J. Pockros P. Galati JS. Frazier LM. Alqahtani S. Sulkowski MS. Vainorius M. Akushevich L. Fried MW. Zeuzem S. Gut 2017; 66: 1844
- 4a Marquez V.-E. Lim M.-I. Med. Chem. Rev. 1986; 6: 1
- 4b Marquez V.-E. In Advances in Antiviral Drug Design . De Clercq E. JAI Press Inc; London: 1996: 89
- 5a Daluge SM. Good SS. Faletto MB. Miller WH. St Clair MH. Boone LR. Tisdale M. Parry NR. Reardon JE. Dornsife RE. Averett DR. Krenitsky T. Antimicrob. Agents Chemother. 1997; 41: 1082
- 5b Daluge SM. Martin MT. Sickles BR. Livingston DA. Nucleosides, Nucleotides Nucleic Acids 2000; 19: 297
- 5c Faletto MB. Miller WH. Garvey EP. St Clair MH. Daluge SM. Good SS. Antimicrob. Agents Chemother. 1997; 41: 1099
- 6a Bisacchi GS. Chao ST. Bachard C. Daris JP. Innaimo S. Jacobs GA. Kocy O. Lapointe P. Martel A. Mechant Z. Slusachyk WA. Sundeen JE. Young MG. Colonno R. Zahler R. Bioorg. Med. Chem. Lett. 1997; 7: 127
- 6b Levine S. Hernandez D. Yamanaka G. Zhang S. Rose R. Weinheimer S. Colonno RJ. Antimicrob. Agents Chemother. 2002; 46: 2525
- 7a Santana L. Teijeira M. Uriarte E. Balzarini J. De Clercq E. Nucleosides, Nucleotides 1995; 14: 521
- 7b Ludek OR. Krämer T. Balzarini J. Meier C. Synthesis 2006; 1313
- 8 Theil F. Ballschuh S. Flatau S. von Janta-Lipinski M. Matthes E. Med. Chem. 1998; 6: 701
- 9 Biggadike K. Borthwick AD. Evans D. Exall AM. Kirk BE. Roberts SM. Stephenson L. Youds P. J. Chem. Soc., Perkin Trans. 1 1988; 539
- 10a Kappe CO. Angew. Chem. Int. Ed. 2004; 43: 6250
- 10b Caddick S. Tetrahedron 1995; 51: 10403
- 10c Steinreiber A. Stadler A. Mayer SF. Faber K. Kappe CO. Tetrahedron Lett. 2001; 42: 6283
- 10d Garcia-Rubiño ME. Núñez-Carretero MC. Choquesillo-Lazarte D. García-Ruiz JM. Madrid Y. Campos JM. RSV Adv. 2014; 4: 22425
- 10e Radi M. Rao JR. Jha AK. Chu CK. Nucleosides, Nucleotides Nucleic Acids 2009; 28: 504
- 11 Weising S. Torquati I. Meier C. Synthesis 2018; 50: 1264
- 12a Ludek OR. Meier C. Synlett 2005; 3145
- 12b Ludek OR. Meier C. Synlett 2006; 324
- 12c Ludek OR. Meier C. Eur. J. Org. Chem. 2006; 941
- 13 Pitsch S. Wendeborn S. Krishnamurthy R. Holzner A. Minton M. Bolli M. Miculca C. Windhab N. Micura R. Stanek M. Jaun B. Eschenmoser A. Helv. Chim. Acta 2003; 86: 4270
- 14a Webb TR. Mitsuya H. Broder S. J. Med. Chem. 1988; 31: 1475
- 14b Ioannidis P. Classon B. Samuelsson B. Kvarnström I. Nucleosides, Nucleotides 1993; 12: 865
- 14c Mahler M. Reichardt B. Hartjen P. van Lunzen J. Meier C. Chem. Eur. J. 2012; 18: 11046
- 15a Asami M. Takahashi J. Inoue S. Tetrahedron: Asymmetry 1994; 5: 1649
- 15b Brown B. Hegedus LS. J. Org. Chem. 2000; 65: 1865
- 17a Santana L. Teijeira M. Uriarte E. Teran C. Casellato U. Graziani R. Nucleosides, Nucleotides 1996; 15: 1179
- 17b Santana L. Teijeira M. Uriarte E. Balzarini J. De Clercq E. Bioorg. Med. Chem. Lett. 1998; 8: 1349
- 17c Estrada E. Uriarte E. Montero A. Teijeira M. Santana L. De Clercq E. J. Med. Chem. 2000; 43: 1975
- 17d Santana L. Teijeira M. Teran C. Uriarte E. Vina D. Synthesis 2001; 1532
- 17e Martinez-Bisbal MC. Vilar S. Teijeira M. Celda B. Uriarte E. Santana L. Struct. Chem. 2006; 17: 465
- 18 Johnson DC. Widlanski TS. Org. Lett. 2004; 6: 4643
- 19 Kolb HC. VanNieuwenhze MS. Sharpless KB. Chem. Rev. 1994; 94: 2483
- 20 Gosselin G. Griffe L. Meillon J.-C. Storer R. Tetrahedron 2006; 62: 906