Abstract
Receptive macrocycles constitute a large spectrum of compounds involving both artificial as well as naturally occurring substances such as crown ethers, cryptands, cyclophanes, porphyrins, and macrolides.1 These compounds play an important role in the exciting area of host-guest supramolecular chemistry. Our interest in the field was initiated by some of our salient observations during the total synthesis of a natural and potassium ion-receptive macrocycle, namely, nonactin.2 After the accomplishment of the total synthesis, we soon recognized the importance of novel, efficient macrocyclization methods and focus our efforts on the design and synthesis of various artificial receptive macrocyclic systems. In this chapter, we present our synthetic results towards the natural 32-membered macrocyclic nonactin and other artificial macrocycles based on our cycloadditive macrocyclization and condensation methods. We also describe herein the molecular recognition study of our host systems with many guest molecules and our ongoing project on the design and synthesis of various photoresponsive and self-responsive molecular systems.
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(a)T. A. Robbins, C. B. Knobler, D. R. Bellew, and D. J. Cram, J. Am. Chem. Soc. 1994, 116, 111. (b) D. J. Cram. Nature 1992, 356, 29. (c) T. K. Park, and J. Rebek, Jr., Angew. Chem., Int. Ed. Engl. 1990, 29, 245. (d) Q. Feng, T. K. Park, and J. Rebek, Jr., Science 1992, 256, 1179. (e) E. Fan, S. A. Van Arman, S. Kincaid, and A. D. Hamilton, J. Am. Chem. Soc. 1993, 115, 369. (f) J. Yang, E. Fan, S. J. Geib, and A. D. Hamilton, ibid 1993, 115, 5314. (g) F. Vögtle, Supramolecular Chemistry (Wiely, New York, 1991). (h) H.-J. Schneider, and H. Dürr, Frontiers in Supramolecular Organic Chemistry and Photochemistry (VCH, Weinheim, 1991). (i) J. L. Atwood, Inclusion Phenomena and Molecular Recognition (Plenum Press, New York, 1990).
(a)R. Corbaz, L. Ettlinger, E. Gaumann, W. Keller-Schien, F. Kradolfer, L. Neipp, V. Prelog, and H. Zahner, Helc. Chim. Acta 1995, 38, 1445. (b) J. Dominquez, J. D. Dunitz, H. Gerlach, and V. Prelog, ibid 1962, 45, 129. (c) H. Gerlach, and V. Prelog, Liebigs Ann. Chem. 1963, 669, 121. (d) M. Dobler, Ionophores and their structure (Wiley, New York, 1981). (e) B. T. Kilbourn, J. D. Dunitz, L. A. R. Pioda, and W. Simon, J. Mol. Bio. 1967, 30, 559.
(a)J. Y. Lee, and B. H. Kim. Tetrahedron Lett. 1995, 41, 4177. (b) J. Y. Lee, and B. H. Kim. Tetrahedron 1996, 52, 571.
J. H. Prestegard, and S. I. Chan, J. Am. Chem. Soc. 1970, 92, 4440.
(a)P. A. Bartlett, and K. K. Jemstedt, Tetrahedron Lett. 1980, 21, 1607. (b) B. H. Kim, and J. Y. Lee, ibid 1992, 33, 2557. (c) B. H. Kim, and J. Y. Lee, ibid 1993, 34, 1609. (d) I. Fleming, and S. K. Ghosh, J. Chem. Soc. Chem. Commun. 1994, 2285, (e) M. Ahmar, C. Duyck, and I. Fleming, Pure & Appl. Chem. 1994, 66, 2049. (f) G. Solladié, and C. Dominguez, J. Org. Chem. 1994, 59, 3898 and references cited therein.
B. Dietrich, P. Viout, and J.-M. Lehn, Macrocyclic Chemistry (VCH, Weinheim, 1993).
B. H. Kim, E. J. Jeong, and W. H. Jung. J. Am. Chem. Soc. 1995, 117, 6390.
R. Huisgen, Angew. Chem., Int. Ed. Engl. 1963, 2, 565.
C. W. Lee, G. T. Hwang, and B. H. Kim, Tetrahedron Lett. 2000, 41, 4177.
G. T. Hwang, and B. H. Kim, Tetrahedron Lett. ibid. 2000, 41, 10055.
D. M. Rudkevich, W. Verboom, and D. N. Reinhoudt, J. Org. Chem. 1994, 59, 3683.
G. T. Hwang, and B. H. Kim, Synth. Commun. 2000, 30, 4205.
G. T. Hwang, and B. H. Kim, Tetrahedron Lett. 2000, 41, 5917.
Z. Zhong, A. Ikeda, and S. Shinkai, J. Am. Chem. Soc. 1999, 121, 11906.
a)P. M. S. Monk, The Viologens (John Wiley & Sons Ltd, Chichester, 1998). b) M. Asakawa, C. L. Brown, S. Menzer, F. M. Raymo, J. F. Stoddart, and D. J. Williams, J. Am. Chem. Soc. 1997, 119, 2614. c) D. B. Amabilino, P. R. Ashton, S. E. Boyd, J. Y. Lee, S. Menzer, J. F. Stoddart, and D. J. Williams, Angew. Chem., Int. Ed. Engl. 1997, 36, 2070.
R. S. Macomber, J. Chem. Educ. 1992, 69, 375.
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Hyean Kim, B., Hwang, G.T., Kim, S.J. (2003). Receptive and Responsive Molecules: Design, Syntehsis, and Evaluation. In: Geckeler, K.E. (eds) Advanced Macromolecular and Supramolecular Materials and Processes. Springer, Boston, MA. https://doi.org/10.1007/978-1-4419-8495-1_6
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DOI: https://doi.org/10.1007/978-1-4419-8495-1_6
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