Synthesis of a shape-persistent macrocycle with intraannular carboxylic acid groups

Tetrahedron

Volumn 59, Issue 47, 2003, Pages 9441-9446

  Fischer, Matthias ^a   Höger, Sigurd ^a,b  

^a MAX PLANCK INSTITUTE FOR POLYMER RESEARCH   (Germany)

^b UNIVERSITY OF KARLSRUHE   (Germany)

Author keywords

Cyclisation; Macrocycles; Supramolecular chemistry

Indexed keywords

4 TERT BUTYL 2,6 DIIDO 1 (2 METHYLBUTOXY)BENZENE; ACETYLENE DERIVATIVE; ACID; ALKYL GROUP; CARBOXYLIC ACID DERIVATIVE; MACROCYCLIC COMPOUND; METHYL 4 (TERT BUTYL 2,6 DIIODOPHENOXY)BUTYRATE; METHYL 4 [2,6 BIS[2 (2,5 DIPROPYLOXY 4 ETHYNYLPHENYL)ETHYNYL] 4 TERT BUTYLPHENOXY]BUTYRATE; METHYL 4 [2,6 BIS[2 [2,5 DIPROPYLOXY 4 (2 TRIISOPROPYLSILYLETHYNYL)PHENYL]ETHYNYL] 4 TERT BUTYLPHENOXY]BUTYRATE; METHYL 4 [2,6 BIS[2 [2,5 DIPROPYLOXY 4 [2 [2 (2 METHYLBUTOXY) 3 (2 TRIMETHYLSILYLETHYNYL) 5 TERT BUTYLPHENYL]ETHYNYL]PHENYL]ETHYNYL] 4 TERT BUTYLPHENOXY]BUTYRATE; METHYL 4 [2,6 BIS[2 [2,5 DIPROPYLOXY 4 [2 [2 (2 METHYLBUTOXY) 3 ETHYNYL 5 TERT BUTYLPHENYL]ETHYNYL]PHENYL]ETHYNYL] 4 TERT BUTYLPHENOXY]BUTYRATE; METHYL 4 [2,6 BIS[2 [2,5 DIPROPYLOXY 4 [2 [2 (2 METHYLBUTOXY) 3 IODO 5 TERT BUTYLPHENYL]ETHYNYL]PHENYL]ETHYNYL] 4 TERT BUTYLPHENOXY]BUTYRATE; PHENYL GROUP; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; HYDROLYSIS; OXIDATION; PRIORITY JOURNAL; SOLUBILITY; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0142153343     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2003.09.045     Document Type: Article

References (29)

1. Moore J.S. Acc. Chem. Res. 30:1997;402-413.
2. Höger S. J. Polym. Sci., Part A: Polym. Chem. 37:1999;2685-2698.
3. Haley M.M., Pak J.J., Brand S.C. Top. Curr. Chem. 201:1999;81-130.
4. Grave C., Schlüter A.D. Eur. J. Org. Chem. 2002;3075-3098.
5. Vögtle F., Neumann P. Tetrahedron. 26:1970;5299-5318.
6. Weber E., Vögtle F. Angew. Chem. 86:1974;126-127. Angew. Chem. Int. Ed. Engl. 1974, 13, 149-150.
7. Anderson H.L., Sanders J.K.M. J. Chem. Soc. Chem. Commun. 1992;946-947.
8. Anderson S., Neidlein U., Gramlich V., Diederich F. Angew. Chem. 107:1995;1722-1726. Angew. Chem. Int. Ed. Engl. 1995, 34, 1596-1600.
9. Morrison D.L., Höger S. J. Chem. Soc. Chem. Commun. 1996;2313-2314.
10. Tobe Y., Utsumi N., Kawabata K., Nagano A., Naemura K. Angew. Chem. 110:1998;1347-1349. Angew. Chem. Int. Ed. Engl. 1998, 37, 1285-1287.
11. Hosokawa Y., Kawase T., Oda M. J. Chem. Soc. Chem. Commun. 2001;1948-1949.
12. Höger S. Macromol. Symp. 142:1999;185-191.
13. Höger S., Meckenstock A.-D., Pellen H. J. Org. Chem. 62:1997;4556-4557.
14. Höger S., Bonrad K., Karcher L., Meckenstock A.-D. J. Org. Chem. 65:2000;1588-1589.
15. Höger S., Bonrad K., Mourran A., Beginn U., Möller M. J. Am. Chem. Soc. 123:2001;5651-5659.
16. Höger S., Enkelmann V. Angew. Chem. 107:1995;2917-2929. Angew. Chem. Int. Ed. Engl. 1995, 34, 2713-2716.
17. Höger S., Meckenstock A.-D., Müller S. Chem. Eur. J. 4:1998;2423-2434.
18. Höger S., Enkelmann V., Bonrad K., Tschierske C. Angew. Chem. 112:2000;2355-2358. Angew. Chem. Int. Ed. Engl. 2000, 39, 2267-2270.
19. Höger S., Morrison D.L., Enkelmann V. J. Am. Chem. Soc. 124:2002;6734-6736.
20. Höger S., Meckenstock A.-D. Chem. Eur. J. 5:1999;1686-1691.
21. Fischer M., Höger S. Eur. J. Org. Chem. 2003;441-446.
22. Pan Z., Still W.C. Tetrahedron Lett. 37:1996;8699-8702.
23. Jensen K.B., Braxmeier T.M., Demarcus M., Frey J.G., Kilburn J.D. Chem. Eur. J. 8:2002;1300-1309.
24. Rosselli S., Ramminger A.-D., Wagner T., Silier B., Wiegand S., Häußler W., Lieser G., Scheumann V., Höger S. Angew. Chem. 113:2001;3234-3237. Angew. Chem. Int. Ed. Engl. 2001, 40, 3138-3141.
25. Höger S., Bonrad K., Rosselli S., Ramminger A.-D., Wagner T., Silier B., Wiegand S., Häußler W., Lieser G., Scheumann V. Macromol. Symp. 177:2002;185-191.
26. Alternatively, side groups can be attached at the outside of the ring so that free acids can be kept in solution and further functionalized: Höger, S.; Ziegler, A. In preparation.
27. In further projects towards intraannular functionalyzed macrocycles using the excess strategy we used a larger excess of the diiodo compound (7-10-fold) and obtained in that cases higher yields (up to 80%).
28. Fischer, M.; Höger, S. Unpublished. Surprisingly, a similar compound with only one intraannular hexanoic acid group is readily soluble, even without additional intraannular groups (cit. Ref. 20).
29. Rosselli S., Ramminger A.-D., Wagner T., Lieser G., Höger S. Chem. Eur. J. 9:2003;3481-3491.