Improved synthesis of methyl 7,7-ethylenedioxy-3-methyl-9-oxobicyclo[3.3.1]non-3-ene-1-carboxylate, intermediate for the synthesis of Huperzine A analogues

Synthetic Communications

Volumn 26, Issue 1, 1996, Pages 9-18

  Camps, Pelayo ^a   Contreras, Joan ^a   Font Bardia, Mercè ^a   Solans, Xavier ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

BICYCLO[3.3.1]NONANE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY; X RAY DIFFRACTION;

EID: 0030023667     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1080/00397919608003857     Document Type: Article

References (23)

1. For syntheses of Huperzine A and analogues modified at the carbocyclic moiety, see: 1a) Xia, Y. and Kozikowski, A. P. J. Am. Chem. Soc. 1989, 111, 116. 1b) Qian, L. and Ji, R. Tetrahedron Lett. 1989, 30, 2089. 1c) Kozikowski, A. P.; Yamada, F.; Tang, X. C. and Hanin, I. Tetrahedron Lett. 1990, 31, 6159. 1d) Yamada, F.; Kozikowski, A. P.; Reddy, E. R.; Pang, Y.-P.; Miller, J. H. and McKinney, M. J. Am. Chem. Soc. 1991, 113, 4695. 1e) Kozikowski, A. P.; Xia, Y.; Reddy, E. R.; Tückmantel, W.; Hanin, I. and Tang, X. C. J. Org. Chem. 1991, 56, 4636. 1f) Kozikowski, A. P.; Yamada, F.; Pang, Y.-P. Tetrahedron Lett. 1992, 33, 2653. 1g) Campiani, G.; Sun, L.-Q.; Kozikowski, A. P.; Aagaard, P. and McKinney, M. J. Org. Chem. 1993, 58, 7660. 1h) Kozikowski, A. P.; Campiani, G.; Aagaard, P. and McKinney, M. J. Chem. Soc. Chem., Commun. 1993, 86o. 1i) He, X. C.; Wang, Z. Y.; Li, Y., L.; Xu, Z. R. and Bai, D. L. Chinese Chem. Lett. 1993, 4, 597. 1j) He, X. C.; Xu, Z. R.; Li, Y., L.; Wang, Z. Y. and Bai, D. L. Chinese Chem. Lett. 1994, 5, 471.
2. For syntheses of Huperzine A and analogues modified at the carbocyclic moiety, see: 1a) Xia, Y. and Kozikowski, A. P. J. Am. Chem. Soc. 1989, 111, 116. 1b) Qian, L. and Ji, R. Tetrahedron Lett. 1989, 30, 2089. 1c) Kozikowski, A. P.; Yamada, F.; Tang, X. C. and Hanin, I. Tetrahedron Lett. 1990, 31, 6159. 1d) Yamada, F.; Kozikowski, A. P.; Reddy, E. R.; Pang, Y.-P.; Miller, J. H. and McKinney, M. J. Am. Chem. Soc. 1991, 113, 4695. 1e) Kozikowski, A. P.; Xia, Y.; Reddy, E. R.; Tückmantel, W.; Hanin, I. and Tang, X. C. J. Org. Chem. 1991, 56, 4636. 1f) Kozikowski, A. P.; Yamada, F.; Pang, Y.-P. Tetrahedron Lett. 1992, 33, 2653. 1g) Campiani, G.; Sun, L.-Q.; Kozikowski, A. P.; Aagaard, P. and McKinney, M. J. Org. Chem. 1993, 58, 7660. 1h) Kozikowski, A. P.; Campiani, G.; Aagaard, P. and McKinney, M. J. Chem. Soc. Chem., Commun. 1993, 86o. 1i) He, X. C.; Wang, Z. Y.; Li, Y., L.; Xu, Z. R. and Bai, D. L. Chinese Chem. Lett. 1993, 4, 597. 1j) He, X. C.; Xu, Z. R.; Li, Y., L.; Wang, Z. Y. and Bai, D. L. Chinese Chem. Lett. 1994, 5, 471.
3. For syntheses of Huperzine A and analogues modified at the carbocyclic moiety, see: 1a) Xia, Y. and Kozikowski, A. P. J. Am. Chem. Soc. 1989, 111, 116. 1b) Qian, L. and Ji, R. Tetrahedron Lett. 1989, 30, 2089. 1c) Kozikowski, A. P.; Yamada, F.; Tang, X. C. and Hanin, I. Tetrahedron Lett. 1990, 31, 6159. 1d) Yamada, F.; Kozikowski, A. P.; Reddy, E. R.; Pang, Y.-P.; Miller, J. H. and McKinney, M. J. Am. Chem. Soc. 1991, 113, 4695. 1e) Kozikowski, A. P.; Xia, Y.; Reddy, E. R.; Tückmantel, W.; Hanin, I. and Tang, X. C. J. Org. Chem. 1991, 56, 4636. 1f) Kozikowski, A. P.; Yamada, F.; Pang, Y.-P. Tetrahedron Lett. 1992, 33, 2653. 1g) Campiani, G.; Sun, L.-Q.; Kozikowski, A. P.; Aagaard, P. and McKinney, M. J. Org. Chem. 1993, 58, 7660. 1h) Kozikowski, A. P.; Campiani, G.; Aagaard, P. and McKinney, M. J. Chem. Soc. Chem., Commun. 1993, 86o. 1i) He, X. C.; Wang, Z. Y.; Li, Y., L.; Xu, Z. R. and Bai, D. L. Chinese Chem. Lett. 1993, 4, 597. 1j) He, X. C.; Xu, Z. R.; Li, Y., L.; Wang, Z. Y. and Bai, D. L. Chinese Chem. Lett. 1994, 5, 471.
4. For syntheses of Huperzine A and analogues modified at the carbocyclic moiety, see: 1a) Xia, Y. and Kozikowski, A. P. J. Am. Chem. Soc. 1989, 111, 116. 1b) Qian, L. and Ji, R. Tetrahedron Lett. 1989, 30, 2089. 1c) Kozikowski, A. P.; Yamada, F.; Tang, X. C. and Hanin, I. Tetrahedron Lett. 1990, 31, 6159. 1d) Yamada, F.; Kozikowski, A. P.; Reddy, E. R.; Pang, Y.-P.; Miller, J. H. and McKinney, M. J. Am. Chem. Soc. 1991, 113, 4695. 1e) Kozikowski, A. P.; Xia, Y.; Reddy, E. R.; Tückmantel, W.; Hanin, I. and Tang, X. C. J. Org. Chem. 1991, 56, 4636. 1f) Kozikowski, A. P.; Yamada, F.; Pang, Y.-P. Tetrahedron Lett. 1992, 33, 2653. 1g) Campiani, G.; Sun, L.-Q.; Kozikowski, A. P.; Aagaard, P. and McKinney, M. J. Org. Chem. 1993, 58, 7660. 1h) Kozikowski, A. P.; Campiani, G.; Aagaard, P. and McKinney, M. J. Chem. Soc. Chem., Commun. 1993, 86o. 1i) He, X. C.; Wang, Z. Y.; Li, Y., L.; Xu, Z. R. and Bai, D. L. Chinese Chem. Lett. 1993, 4, 597. 1j) He, X. C.; Xu, Z. R.; Li, Y., L.; Wang, Z. Y. and Bai, D. L. Chinese Chem. Lett. 1994, 5, 471.
5. For syntheses of Huperzine A and analogues modified at the carbocyclic moiety, see: 1a) Xia, Y. and Kozikowski, A. P. J. Am. Chem. Soc. 1989, 111, 116. 1b) Qian, L. and Ji, R. Tetrahedron Lett. 1989, 30, 2089. 1c) Kozikowski, A. P.; Yamada, F.; Tang, X. C. and Hanin, I. Tetrahedron Lett. 1990, 31, 6159. 1d) Yamada, F.; Kozikowski, A. P.; Reddy, E. R.; Pang, Y.-P.; Miller, J. H. and McKinney, M. J. Am. Chem. Soc. 1991, 113, 4695. 1e) Kozikowski, A. P.; Xia, Y.; Reddy, E. R.; Tückmantel, W.; Hanin, I. and Tang, X. C. J. Org. Chem. 1991, 56, 4636. 1f) Kozikowski, A. P.; Yamada, F.; Pang, Y.-P. Tetrahedron Lett. 1992, 33, 2653. 1g) Campiani, G.; Sun, L.-Q.; Kozikowski, A. P.; Aagaard, P. and McKinney, M. J. Org. Chem. 1993, 58, 7660. 1h) Kozikowski, A. P.; Campiani, G.; Aagaard, P. and McKinney, M. J. Chem. Soc. Chem., Commun. 1993, 86o. 1i) He, X. C.; Wang, Z. Y.; Li, Y., L.; Xu, Z. R. and Bai, D. L. Chinese Chem. Lett. 1993, 4, 597. 1j) He, X. C.; Xu, Z. R.; Li, Y., L.; Wang, Z. Y. and Bai, D. L. Chinese Chem. Lett. 1994, 5, 471.
6. For syntheses of Huperzine A and analogues modified at the carbocyclic moiety, see: 1a) Xia, Y. and Kozikowski, A. P. J. Am. Chem. Soc. 1989, 111, 116. 1b) Qian, L. and Ji, R. Tetrahedron Lett. 1989, 30, 2089. 1c) Kozikowski, A. P.; Yamada, F.; Tang, X. C. and Hanin, I. Tetrahedron Lett. 1990, 31, 6159. 1d) Yamada, F.; Kozikowski, A. P.; Reddy, E. R.; Pang, Y.-P.; Miller, J. H. and McKinney, M. J. Am. Chem. Soc. 1991, 113, 4695. 1e) Kozikowski, A. P.; Xia, Y.; Reddy, E. R.; Tückmantel, W.; Hanin, I. and Tang, X. C. J. Org. Chem. 1991, 56, 4636. 1f) Kozikowski, A. P.; Yamada, F.; Pang, Y.-P. Tetrahedron Lett. 1992, 33, 2653. 1g) Campiani, G.; Sun, L.-Q.; Kozikowski, A. P.; Aagaard, P. and McKinney, M. J. Org. Chem. 1993, 58, 7660. 1h) Kozikowski, A. P.; Campiani, G.; Aagaard, P. and McKinney, M. J. Chem. Soc. Chem., Commun. 1993, 86o. 1i) He, X. C.; Wang, Z. Y.; Li, Y., L.; Xu, Z. R. and Bai, D. L. Chinese Chem. Lett. 1993, 4, 597. 1j) He, X. C.; Xu, Z. R.; Li, Y., L.; Wang, Z. Y. and Bai, D. L. Chinese Chem. Lett. 1994, 5, 471.
7. For syntheses of Huperzine A and analogues modified at the carbocyclic moiety, see: 1a) Xia, Y. and Kozikowski, A. P. J. Am. Chem. Soc. 1989, 111, 116. 1b) Qian, L. and Ji, R. Tetrahedron Lett. 1989, 30, 2089. 1c) Kozikowski, A. P.; Yamada, F.; Tang, X. C. and Hanin, I. Tetrahedron Lett. 1990, 31, 6159. 1d) Yamada, F.; Kozikowski, A. P.; Reddy, E. R.; Pang, Y.-P.; Miller, J. H. and McKinney, M. J. Am. Chem. Soc. 1991, 113, 4695. 1e) Kozikowski, A. P.; Xia, Y.; Reddy, E. R.; Tückmantel, W.; Hanin, I. and Tang, X. C. J. Org. Chem. 1991, 56, 4636. 1f) Kozikowski, A. P.; Yamada, F.; Pang, Y.-P. Tetrahedron Lett. 1992, 33, 2653. 1g) Campiani, G.; Sun, L.-Q.; Kozikowski, A. P.; Aagaard, P. and McKinney, M. J. Org. Chem. 1993, 58, 7660. 1h) Kozikowski, A. P.; Campiani, G.; Aagaard, P. and McKinney, M. J. Chem. Soc. Chem., Commun. 1993, 86o. 1i) He, X. C.; Wang, Z. Y.; Li, Y., L.; Xu, Z. R. and Bai, D. L. Chinese Chem. Lett. 1993, 4, 597. 1j) He, X. C.; Xu, Z. R.; Li, Y., L.; Wang, Z. Y. and Bai, D. L. Chinese Chem. Lett. 1994, 5, 471.
8. For syntheses of Huperzine A and analogues modified at the carbocyclic moiety, see: 1a) Xia, Y. and Kozikowski, A. P. J. Am. Chem. Soc. 1989, 111, 116. 1b) Qian, L. and Ji, R. Tetrahedron Lett. 1989, 30, 2089. 1c) Kozikowski, A. P.; Yamada, F.; Tang, X. C. and Hanin, I. Tetrahedron Lett. 1990, 31, 6159. 1d) Yamada, F.; Kozikowski, A. P.; Reddy, E. R.; Pang, Y.-P.; Miller, J. H. and McKinney, M. J. Am. Chem. Soc. 1991, 113, 4695. 1e) Kozikowski, A. P.; Xia, Y.; Reddy, E. R.; Tückmantel, W.; Hanin, I. and Tang, X. C. J. Org. Chem. 1991, 56, 4636. 1f) Kozikowski, A. P.; Yamada, F.; Pang, Y.-P. Tetrahedron Lett. 1992, 33, 2653. 1g) Campiani, G.; Sun, L.-Q.; Kozikowski, A. P.; Aagaard, P. and McKinney, M. J. Org. Chem. 1993, 58, 7660. 1h) Kozikowski, A. P.; Campiani, G.; Aagaard, P. and McKinney, M. J. Chem. Soc. Chem., Commun. 1993, 86o. 1i) He, X. C.; Wang, Z. Y.; Li, Y., L.; Xu, Z. R. and Bai, D. L. Chinese Chem. Lett. 1993, 4, 597. 1j) He, X. C.; Xu, Z. R.; Li, Y., L.; Wang, Z. Y. and Bai, D. L. Chinese Chem. Lett. 1994, 5, 471.
9. For syntheses of Huperzine A and analogues modified at the carbocyclic moiety, see: 1a) Xia, Y. and Kozikowski, A. P. J. Am. Chem. Soc. 1989, 111, 116. 1b) Qian, L. and Ji, R. Tetrahedron Lett. 1989, 30, 2089. 1c) Kozikowski, A. P.; Yamada, F.; Tang, X. C. and Hanin, I. Tetrahedron Lett. 1990, 31, 6159. 1d) Yamada, F.; Kozikowski, A. P.; Reddy, E. R.; Pang, Y.-P.; Miller, J. H. and McKinney, M. J. Am. Chem. Soc. 1991, 113, 4695. 1e) Kozikowski, A. P.; Xia, Y.; Reddy, E. R.; Tückmantel, W.; Hanin, I. and Tang, X. C. J. Org. Chem. 1991, 56, 4636. 1f) Kozikowski, A. P.; Yamada, F.; Pang, Y.-P. Tetrahedron Lett. 1992, 33, 2653. 1g) Campiani, G.; Sun, L.-Q.; Kozikowski, A. P.; Aagaard, P. and McKinney, M. J. Org. Chem. 1993, 58, 7660. 1h) Kozikowski, A. P.; Campiani, G.; Aagaard, P. and McKinney, M. J. Chem. Soc. Chem., Commun. 1993, 86o. 1i) He, X. C.; Wang, Z. Y.; Li, Y., L.; Xu, Z. R. and Bai, D. L. Chinese Chem. Lett. 1993, 4, 597. 1j) He, X. C.; Xu, Z. R.; Li, Y., L.; Wang, Z. Y. and Bai, D. L. Chinese Chem. Lett. 1994, 5, 471.
10. For syntheses of Huperzine A and analogues modified at the carbocyclic moiety, see: 1a) Xia, Y. and Kozikowski, A. P. J. Am. Chem. Soc. 1989, 111, 116. 1b) Qian, L. and Ji, R. Tetrahedron Lett. 1989, 30, 2089. 1c) Kozikowski, A. P.; Yamada, F.; Tang, X. C. and Hanin, I. Tetrahedron Lett. 1990, 31, 6159. 1d) Yamada, F.; Kozikowski, A. P.; Reddy, E. R.; Pang, Y.-P.; Miller, J. H. and McKinney, M. J. Am. Chem. Soc. 1991, 113, 4695. 1e) Kozikowski, A. P.; Xia, Y.; Reddy, E. R.; Tückmantel, W.; Hanin, I. and Tang, X. C. J. Org. Chem. 1991, 56, 4636. 1f) Kozikowski, A. P.; Yamada, F.; Pang, Y.-P. Tetrahedron Lett. 1992, 33, 2653. 1g) Campiani, G.; Sun, L.-Q.; Kozikowski, A. P.; Aagaard, P. and McKinney, M. J. Org. Chem. 1993, 58, 7660. 1h) Kozikowski, A. P.; Campiani, G.; Aagaard, P. and McKinney, M. J. Chem. Soc. Chem., Commun. 1993, 86o. 1i) He, X. C.; Wang, Z. Y.; Li, Y., L.; Xu, Z. R. and Bai, D. L. Chinese Chem. Lett. 1993, 4, 597. 1j) He, X. C.; Xu, Z. R.; Li, Y., L.; Wang, Z. Y. and Bai, D. L. Chinese Chem. Lett. 1994, 5, 471.
11. Aguado, F.; Badía, A.; Baños, J. E.; Bosch, F.; Bozzo, C.; Camps, P.; Contreras, J.; Dierssen, M.; Escolano, C.; Görbig, D. M.; Muñoz-Torrero, D.; Pujol, M. D.; Simón, M.; Vázquez, M. T. and Vivas, N. M. Eur. J. Med. Chem. 1994, 29, 205.
12. For the synthesis of analogues of Huperzine A modified at the heterocyclic moiety, see: 3a) Xia, Y.; Reddy, A. R. and Kozikowski, A. P. Tetrahedron Lett. 1989, 30, 3291. 3b) Kozikowski, A. P.; Tückmantel, W.; Saxena, A. and Doctor, B. P. Helv. Chim. Acta 1994, 77, 1256. 3c) Kozikowski, A. P.; Campiani, G. and Tückmantel, W. Heterocycles 1994, 39, 101. 3d) Kozikowski, A. P.; Campiani, G.; Saxena, A. and Doctor, B. P. J. Chem. Soc., Chem. Commun. 1995, 283.
13. For the synthesis of analogues of Huperzine A modified at the heterocyclic moiety, see: 3a) Xia, Y.; Reddy, A. R. and Kozikowski, A. P. Tetrahedron Lett. 1989, 30, 3291. 3b) Kozikowski, A. P.; Tückmantel, W.; Saxena, A. and Doctor, B. P. Helv. Chim. Acta 1994, 77, 1256. 3c) Kozikowski, A. P.; Campiani, G. and Tückmantel, W. Heterocycles 1994, 39, 101. 3d) Kozikowski, A. P.; Campiani, G.; Saxena, A. and Doctor, B. P. J. Chem. Soc., Chem. Commun. 1995, 283.
14. For the synthesis of analogues of Huperzine A modified at the heterocyclic moiety, see: 3a) Xia, Y.; Reddy, A. R. and Kozikowski, A. P. Tetrahedron Lett. 1989, 30, 3291. 3b) Kozikowski, A. P.; Tückmantel, W.; Saxena, A. and Doctor, B. P. Helv. Chim. Acta 1994, 77, 1256. 3c) Kozikowski, A. P.; Campiani, G. and Tückmantel, W. Heterocycles 1994, 39, 101. 3d) Kozikowski, A. P.; Campiani, G.; Saxena, A. and Doctor, B. P. J. Chem. Soc., Chem. Commun. 1995, 283.
15. For the synthesis of analogues of Huperzine A modified at the heterocyclic moiety, see: 3a) Xia, Y.; Reddy, A. R. and Kozikowski, A. P. Tetrahedron Lett. 1989, 30, 3291. 3b) Kozikowski, A. P.; Tückmantel, W.; Saxena, A. and Doctor, B. P. Helv. Chim. Acta 1994, 77, 1256. 3c) Kozikowski, A. P.; Campiani, G. and Tückmantel, W. Heterocycles 1994, 39, 101. 3d) Kozikowski, A. P.; Campiani, G.; Saxena, A. and Doctor, B. P. J. Chem. Soc., Chem. Commun. 1995, 283.
16. Lukes, R. M.; Poos, G. I. and Sarett, L. H. J. Am. Chem. Soc. 1952, 74, 1401.
17. Kraus, G. A.; Hansen, J. and Vines, D. Synth. Commun. 1992, 22, 2625.
18. Zefirov, N. S. and Palyulin, V. A. Topics Stereochem. 1991, 20, 171.
19. Aranda, G.; Bernassau, J. M.; Fetizon, M. and Hanna, I. J. Org. Chem. 1985, 50, 1156.
20. Camps, P.; Vázquez, S.; Jaime, C. and Virgili, A. Magn. Reson. Chem. 1994, 32, 210.
21. Sheldrick, G. M. Acta Crystallograr. 1990, A46, 467.
22. Sheldrick, G. M. SHELX-93, Program for Crystal Structure Determinations, 1995, in preparation.
23. International Tables of X-ray Crystallography, Kynoch Press, Birmingham, 1974, vol IV, p. 99-100 and 149.