The "triamino-analogue" of methyl allocholate; a rigid, functionalised scaffold for supramolecular chemistry

Chemical Communications

Volumn , Issue 22, 2006, Pages 2335-2337

  Bhattarai, Khadga M ^a   Del Amo, Vicente ^a   Magro, Germinal ^a   Sisson, Adam L ^a   Joos, Jean Baptiste ^a   Charmant, Jonathan P H ^a   Kantacha, Anob ^a   Davis, Anthony P ^a  

^a UNIVERSITY OF BRISTOL   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; CHOLIC ACID DERIVATIVE;

ARTICLE; BINDING AFFINITY; HYDROGEN BOND; REACTION ANALYSIS; STEREOCHEMISTRY; SUPRAMOLECULAR CHEMISTRY; SYNTHESIS; TRANS ISOMER;

EID: 33744932474     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b602415g     Document Type: Article

References (28)

1. E. Virtanen E. Kolehmainen Eur. J. Org. Chem. 2004 3385
2. R. Maltais M. R. Tremblay L. C. Ciobanu D. Poirier J. Comb. Chem. 2004 6 443
3. S. Matile A. Som N. Sorde Tetrahedron 2004 60 6405
4. A. P. Davis J.-B. Joos Coord. Chem. Rev. 2003 240 143
5. X. X. Zhu M. Nichifor Acc. Chem. Res. 2002 35 539
6. P. B. Savage Eur. J. Org. Chem. 2002 759
7. P. Wallimann T. Marti A. Furer F. Diederich Chem. Rev. 1997 97 1567
8. A. P. Davis, R. P. Bonar-Law and J. K. M. Sanders, in Comprehensive Supramolecular Chemistry, ed., Y. Murakami,, Pergamon, Oxford, 1996, Vol. 4 (Supramolecular Reactivity and Transport: Bioorganic Systems), p. 257
9. A. P. Davis J. J. Perry R. P. Williams J. Am. Chem. Soc. 1997 119 1793
10. J. P. Clare A. J. Ayling J. B. Joos A. L. Sisson G. Magro M. N. Pérez-Payán T. N. Lambert R. Shukla B. D. Smith A. P. Davis J. Am. Chem. Soc. 2005 127 10739
11. B. W. Ding N. Yin Y. Liu J. Cardenas-Garcia R. Evanson T. Cirsak M. J. Fan G. Turin P. B. Savage J. Am. Chem. Soc. 2004 126 13642
12. Y. R. Vandenburg B. D. Smith M. N. Pérez-Payán A. P. Davis J. Am. Chem. Soc. 2000 122 3252
13. Y. A. Cheng T. Suenaga W. C. Still J. Am. Chem. Soc. 1996 118 1813
14. A. Kasal L. Kohout M. Lebl Collect. Czech. Chem. Commun. 1995 60 2147
15. X. T. Zhou A. Rehman C. H. Li P. B. Savage Org. Lett. 2000 2 3015
16. H. De Muynck A. Madder N. Farcy P. J. De Clercq M. N. Pérez-Payán L. M. Öhberg A. P. Davis Angew. Chem., Int. Ed. 2000 39 145
17. B. W. Ding U. Taotofa T. Orsak M. Chadwell P. B. Savage Org. Lett. 2004 6 3433
18. V. del Amo L. Siracusa T. Markidis B. Baragaña K. M. Bhattarai M. Galobardes G. Naredo M. N. Pérez-Payán A. P. Davis Org. Biomol. Chem. 2004 2 3320
19. S. Broderick A. P. Davis R. P. Williams Tetrahedron Lett. 1998 39 6083
20. A. P. Davis M. N. Pérez-Payán Synlett 1999 991
21. V. del Amo K. Bhattarai M. Nissinen K. Rissanen M. N. Pérez-Payán A. P. Davis Synlett 2005 1319
22. C. H. Li A. Rehman N. K. Dalley P. B. Savage Tetrahedron Lett. 1999 40 1861
23. 4a
24. A. Kallner Acta Chem. Scand. 1967 21 322
25. A. L. Sisson V. del Amo Sanchez G. Magro A. M. E. Griffin S. Shah J. P. H. Charmant A. P. Davis Angew. Chem., Int. Ed. 2005 44 6878
26. A. J. Ayling S. Broderick J. P. Clare A. P. Davis M. N. Pérez-Payán M. Lahtinen M. J. Nissinen K. Rissanen Chem.-Eur. J. 2002 8 2197
27. 5c was tested against a more limited series of anions. The binding constants were the same as those for 11 to within experimental error. For further details see Supporting Information
28. We have already differentiated between positions 3 and 7/12, through selective protection of the equatorial 3β-OH in intermediate 7. Further transformations led to an analogue of 9 with the 3α-N protected as azide