Carbocations in action. Design, synthesis, and evaluation of a highly acid-sensitive naphthalene-based backbone amide linker for solid-phase synthesis

Organic Letters

Volumn 8, Issue 25, 2006, Pages 5817-5820

  Pittelkow, Michael ^a   Boas, Ulrik ^a   Christensen, Jørn B ^a  

^a UNIVERSITY OF COPENHAGEN   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33846317777     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol062410j     Document Type: Article

References (23)

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3. (a) Methods of Organic Chemistry; Goodman, M., Felix, A., Moroder, L., Toniolo, C., Eds.; Houben-Weyl, Georg Thieme Verlag: Stuttgart, New York, 2002; Vol. E22a.
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13. Other factors may influence the cleavage properties: Norrby, P.-O.; Jensen, K. J. Int. J. Pept. Res. Ther. 2006, in press.
14. For reviews of BAL handles, see: (a) Alsina, J.; Jensen, K. J.; Albericio, F.; Barany, G. Chem.-Eur. J. 1999, 5, 2787.
15. (b) Alsina, J.; Jensen, K. J.; Songster, M. F.; Vágner, J.; Albericio, F.; Barany, G. In Solid-phase Organic Synthesis; Czarnik, A. W., Ed.; John Wiley & Sons: New York, 2001; Vol. 1, p 121.
16. For an indole-based BAL handle, see: Estep, K. G.; Neipp, C. E.; Stramiello-Stephens, L. M.; Adam, M. D.; Allen, M. P.; Robinson, S.; Roskamp, E. J. J. Org. Chem. 1998, 63, 5300.
17. Jessing, M.; Brandt, M.; Jensen, K. J.; Christensen, J. B.; Boas, U. J. Org. Chem. 2006, 71, 6734.
18. Boas, U.; Christensen, J. B.; Jensen, K. J. J. Comb. Chem. 2004, 6, 497.
19. Pittelkow, M.; Boas, U.; Jessing, M.; Jensen, K. J.; Christensen, J. B. Org. Biomol. Chem. 2005, 3, 508.
20. Boas, U.; Brask, J.; Christensen, J. B.; Jensen, K. J. J. Comb. Chem. 2002, 4, 223.
21. Pittelkow, M.; Christensen, J. B.; Sølling, T. I. Org. Biomol. Chem. 2005, 3, 2441.
22. Our procedure for the synthesis of 1 is similar to: Tanaka, H.; Ohne, Y.; Ogawa, N; Tamura, T. Agric. Biol. Chem. 1963, 27, 48.
23. For a recent and different strategy to 2: McCulloch, M. W. B.; Barrow, R. A. Tetrahedron Lett. 2005, 46, 7619.