Transformation of [6] and [7]metacyclophanols into new strained tricyclic ethers via an intramolecular version of the S(N)2 reaction

Tetrahedron Letters

Volumn 38, Issue 18, 1997, Pages 3267-3270

  Lee, Woo Song ^a   Nagao, Yoshimitsu ^a  

^a UNIVERSITY OF TOKUSHIMA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

POLYCYCLIC HYDROCARBON;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY; X RAY CRYSTALLOGRAPHY;

EID: 0030942292     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00599-6     Document Type: Article

References (15)

1. [6]Metacyclophane: a) Hirano, S.; Hara, H.; Hiyama, T.; Fujita, S.; Nozaki, H. Tetrahedron 1975, 31, 2219.
2. b) Shea, K. J.; Burke, L. D.; Doedens, R. J. J. Am. Chem. Soc. 1985, 707, 5305.
3. [6]Metacycloph-3-ene: c) Goodman, J. L; Berson, J. A. J. Am. Chem. Soc. 1985, 707, 5424.
4. [5]Metacyclophane: d) Turkenburg, L. A. M.; Blok, P. L. M; De Wolf, W. H.; Bickelhaupt, F. Tetrahedron Lett. 1981, 22, 3317.
5. e) Jenneskens, L. W.; De Kanter, F. J. J.; Turkenburg, L. A. M.; DeBoer, H. J. J.; De Wolf, W. H.; Bickelhaupt, F. Tetrahedron 1984, 40, 4413.
6. [4]Metacyclophane: f) Kostermans, G. B. M.; Van Dansik, P.; De Wolf, W. H.; Bickelhaupt, F. J. Am. Chem. Soc. 1987, 709, 7887.
7. g) Kostermans, G. B. M.; Van Dansik, P.; De Wolf, W. H.; Bickelhaupt, F. J. Org. Chem. 1988, 53, 4531.
8. a) Kraakman, P. A.; Valk, J.-M.; Niederlander, H. A. G.; Brouwer, D. B. E.; Bickelhaupt, F. M.; de Wolf, W. H.; Bickelhaupt, F.; Stam, C. H. J. Am. Chem. Soc. 1990, 112, 6638.
9. b) Jenneskens, L. W.; de Boer, H.J. R.; de Wolf, W. H.; Bickelhaupt, F. J. Am. Chem. Soc. 1990, 112, 8941.
10. Lee, W. S.; Jeong, I.-Y.; Shiro, M.; Sano, S.; Nagao, Y. Tetrahedron Lett. 1997, 38, 611.
11. 3, R = 0.062.
12. MM(Discover-CVFF) calculations were performed by using the insight II/Discover 95.0 (MSI/BIOSYM Inc., CA) program.
13. 3, V = 1882.3101 Å3, R = 0.047.
14. 3, R = 0.059.
15. Nakata, T.; Nomura, S.; Matsukura, H. Tetrahedron Lett. 1996, 37, 213.