Regioselective intramolecular-bridging of calix[8]arenes: Unexpected isolation of a doubly-bridged unimolecular capsule-like compound

Tetrahedron Letters

Volumn 37, Issue 10, 1996, Pages 1621-1624

  Ikeda, Atsushi ^a   Akao, Kiyotaka ^a   Harada, Takaaki ^b   Shinkai, Seiji ^a,b  

^a KYUSHU UNIVERSITY   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CALIXARENE; MACROCYCLIC COMPOUND;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 0029875469     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00071-8     Document Type: Article

References (15)

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3. Suzuki, T.; Nakashima, K.; Shinkai, S., Chem. Lett., 1994, 699-702; Atwood, J. L.; Koutsantonis, G. A.; Raston, C. L., Nature, 1994, 368, 229-231.
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5. Neri, P.; Battocolo, E.; Cunsolo, F.; Geraci, C.; Piattelli, M., J. Org. Chem. 1994, 59, 3880-3889; Neri, P.; Geraci, C.; Piattelli, M., J. Org. Chem., 1995, 60, 4126-4135; Cunsolo, F.; Piattelli, M.; Neri, P., J. Chem. Soc., Chem. Commun., 1994, 1917-1918.
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9. The subscript indicates the bridged positions. For example, 1,4 and 1,5-3,7 indicate a 1,4-singly-bridged compound and a 1,5-3,7-doubly-bridged compound, respectively.
10. Similar 1,5-3,7-doubly-bridged calix[8]arenes were synthesized by Neri et al. from tetrabenzylated calix[8]arene: Geraci, C.; Piattelli, M.; Neri, P., Tetrahedron Lett., 1995, 36, 5429-5432.
11. 1,4. These compounds are all identical, 5,11,17,23,29,35,41,47-octa-tert-butyl-49,50,51,52,54,55-hexamethoxycalix[8] arene-53,56-diol.
12. 10 by a block diagonal monomozation method.
13. Allinger, N. L.; Yuh, Y. H.; Lii, J.-H., J. Am., Chem. Soc., 1989, 111, 8551-8566. The MM3(92) programs for the UNIX system were obtained from Technical Utilization Corporation, Inc., 235 Gle Village Court, Powell, OH 43065 (U.S.A.). See manual and references cited therein.
14. Allen, F. H.; Kennard, O.; Watson, D. G.; Brammer, L.; Orpen, A. G.; and Taylor, R., J. Chem. Soc., Perkin Trans. 2, 1987, S1.
15. MOLGRAPH™ is a molecular design support system from DAIKIN Ind. Ltd.