C-nucleosidations with 2,6-diamino-5,8-diaza-7,9-dicarba-purine

Organic Letters

Volumn 5, Issue 12, 2003, Pages 2071-2074

  Han, Bo ^b   Wang, Zhijun ^a   Jaun, Bernhard ^b   Krishnamurthy, Ramanarayanan ^a   Eschenmoser, Albert ^a,b  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

^b ETH ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

2,6 DIAMINO 5,8 DIAZA 7,9 DICARBAPURINE; 2,6 DIAMINOPURINE DERIVATIVE; NUCLEOSIDE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; REACTION ANALYSIS;

2-AMINOPURINE; AZA COMPOUNDS; IMINES; PURINE NUCLEOSIDES; PURINES; TETROSES;

EID: 0141563558     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol030043v     Document Type: Article

References (28)

1. Chemistry of α-Aminonitriles. Part 40. Part 39: ref 4.
2. Miller, S. L.; Orgel, L. E. The Origins of Life on Earth; Prentice Hall Inc.: Englewood Cliffs, New Jersey, 1974.
3. Strecker, A. Liebigs Ann. Chem. 1850, 75, 27; Liebigs Ann. Chem. 1854, 91, 349. Miller, S. L. Science 1953, 117, 528.
4. Strecker, A. Liebigs Ann. Chem. 1850, 75, 27; Liebigs Ann. Chem. 1854, 91, 349. Miller, S. L. Science 1953, 117, 528.
5. Strecker, A. Liebigs Ann. Chem. 1850, 75, 27; Liebigs Ann. Chem. 1854, 91, 349. Miller, S. L. Science 1953, 117, 528.
6. Wang, Z.; Huynh, H. K.; Han, B.; Krishnamurthy, R.; Eschenmoser, A. Org. Lett. 2003, 5, 2067.
7. For reviews on the chemical synthesis of C-nucleosides and C-glucosides see: Hanessian, S.; Peruet, A. G. Adv. Carbohydrate. Chem. Biochem. 1976, 33, 111. Postema, M. H. D. Tetrahedron 1992, 48, 9545.
8. For reviews on the chemical synthesis of C-nucleosides and C-glucosides see: Hanessian, S.; Peruet, A. G. Adv. Carbohydrate. Chem. Biochem. 1976, 33, 111. Postema, M. H. D. Tetrahedron 1992, 48, 9545.
9. Brouwer, A. J.; van der Linden, H. J.; Liskamp, R. M. J. J. Org. Chem. 2000, 65, 1750.
10. Arakawa, Y.; Yoshifuji, S. Chem. Pharm. Bull. 1991, 39, 2219.
11. Folkersen, B. M.; Lundt, I.; Foged, C.; Valsborg, J. S. J. Labelled Compd. Radiopharm. 1999, 42, 1145.
12. Data of 2 and 6 in Supporting Information.
13. 13C NMR spectra; the latter show the single set of signals belonging to the monomer-derived units. This indicates the configuration at the stereogenic carbon centers of the tricycle's inner (six-membered) ring to be all cis, the configuration shown in the formula 6 being the (sterically) more favourable of the two possibilities.
14. 3OD) between H-(C3′) and H-(C1′) in 4b, the product from the deprotection of 3b.
15. +.
16. The higher propensity of pyrroline 7 as compared to that of 2 to form a trimer corresponds to the (presumably) higher reactivity of its imine double bond (less "polarized" carbonyl systems are more, and not less, reactive than more "polarized" systems), as well as to the difference in steric bulk of the substituents.
17. Note that the molar ratio monomer equivalent 7 to 1 is 3:1.
18. Data of 9a and 9b in Supporting Information.
19. 2O solution, respectively.
20. 3 or both, under otherwise identical conditions (TLC).
21. The (polar) products of "decomposition" have not been identified.
22. 4/HOAc (1:1), 98°C, 1 h).
23. The elevated reaction temperature was found to be required to induce the elimination-cyclization step (see Scheme 5).
24. See Supporting Information. The analysis was carried out by Raj K. Chadha, TSRI. Crystallographic data for the structure has been deposited with the Cambridge Crystallographic Data Center as deposition no. CCDC 180980. Copies of the data can be obtained, free of charge, on application to the CCDC, 12 union Road, Cambridge CB12 1EZ UK (fax, + 44 (1233) 336 0333; E-mail, deposit@ccdc.cam.ac.uk).
25. Maqbool, Z.; Hasan, M.; Pott, K. T.; Malik, A.; Zizami, T. A.; Voelter, W. Z. Naturforsch. 1997, B 52, 1383.
26. Except ratio 13:1 = 2:1 and reaction time 65 h.
27. 1H NMR, MS).
28. 6)).