Synthesis of novel tricyclononanes

Tetrahedron Letters

Volumn 38, Issue 30, 1997, Pages 5331-5334

  Kragol, Goran ^a   Mlinarić Majerski, Kata ^a  

^a RUDER BO KOVI INSTITUTE   (Croatia)

Author keywords

[No Author keywords available]

Indexed keywords

AMMONIA; HYDROCARBON; KETONE; LITHIUM;

ARTICLE; DRUG SYNTHESIS; ELECTRON TRANSPORT; PHOTOCHEMISTRY; REDUCTION;

EID: 0343471439     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01165-9     Document Type: Article

References (23)

1. For stereoselective reduction of some polycyclic cyclopropyl ketones see: (a) Norin, T. Acta Chem. Scand. 1963, 17, 738-748; ibid 1965, 19, 1289-1292.
2. For stereoselective reduction of some polycyclic cyclopropyl ketones see: (a) Norin, T. Acta Chem. Scand. 1963, 17, 738-748; ibid 1965, 19, 1289-1292.
3. (b) Dauben, W. G.; Deviny, E. J. J. Org. Chem. 1966, 31, 3794-3798.
4. (c) Shoulders, B. A.; Kwie, W. W.; Klyne, W.; Gardner, P. D. Tetrahedron 1963, 21, 2973-2981.
5. (d) Nickon, A.; Kwasnik, H.; Swartz, T.; Williams, R. O.; DiGiorgio, J. B. J. Am. Chem. Soc. 1965, 87, 1615-1616.
6. (e) House, H. O.; Boots, S. G.; Jones, V. K. J. Org. Chem. 1965, 30, 2519-2527.
7. Batey, R. A.; Motherwell, W. B. Tetrahedron Lett. 1991, 32, 6211-6214.
8. (a) Cassey, J.; Furet, N. Tetrahedron Lett. 1993, 34, 8107-8110.
9. (b) Kirschberg, T.; Mattay, J. Tetrahedron Lett. 1994, 39, 7217-7220.
10. Mlinarić-Majerski, K.; Kragol, G.; Šindler Kulyk, M.; Pavlović, D. Liebigs Ann. 1995, 1885-1889.
11. Šindler-Kulyk, M.; Majerski, Z.; Pavlović, D.; Mlinarić-Majerski, K. Tetrahedron Lett. 1989, 3577-3578.
12. 3,8]nonane skeleta in a protracting syntheses or as a mixture of products (a) by intramolecular photochemical [2+2] cycloadditions : Fröstl, W.; Margaretha, P. Helv. Chim. Acta. 1976, 59, 2244-2248. Martin, S. F.; White J. B. Tetrahedron Lett. 1982, 23, 23-26.; Cruciani, G.; Margaretha P. Helv. Chim. Acta 1990, 73, 288-296.; McMurry, T. B. H.; Work, A.; McKenna, B. J. Chem. Soc., Perkin Trans. 1, 1991, 811-816;
13. 3,8]nonane skeleta in a protracting syntheses or as a mixture of products (a) by intramolecular photochemical [2+2] cycloadditions : Fröstl, W.; Margaretha, P. Helv. Chim. Acta. 1976, 59, 2244-2248. Martin, S. F.; White J. B. Tetrahedron Lett. 1982, 23, 23-26.; Cruciani, G.; Margaretha P. Helv. Chim. Acta 1990, 73, 288-296.; McMurry, T. B. H.; Work, A.; McKenna, B. J. Chem. Soc., Perkin Trans. 1, 1991, 811-816;
14. 3,8]nonane skeleta in a protracting syntheses or as a mixture of products (a) by intramolecular photochemical [2+2] cycloadditions : Fröstl, W.; Margaretha, P. Helv. Chim. Acta. 1976, 59, 2244-2248. Martin, S. F.; White J. B. Tetrahedron Lett. 1982, 23, 23-26.; Cruciani, G.; Margaretha P. Helv. Chim. Acta 1990, 73, 288-296.; McMurry, T. B. H.; Work, A.; McKenna, B. J. Chem. Soc., Perkin Trans. 1, 1991, 811-816;
15. 3,8]nonane skeleta in a protracting syntheses or as a mixture of products (a) by intramolecular photochemical [2+2] cycloadditions : Fröstl, W.; Margaretha, P. Helv. Chim. Acta. 1976, 59, 2244-2248. Martin, S. F.; White J. B. Tetrahedron Lett. 1982, 23, 23-26.; Cruciani, G.; Margaretha P. Helv. Chim. Acta 1990, 73, 288-296.; McMurry, T. B. H.; Work, A.; McKenna, B. J. Chem. Soc., Perkin Trans. 1, 1991, 811-816;
16. (b) by tandem intramolecular Michael-aldol reactions: Ihara, M.; Ohnishi, M.; Takano, M.; Makita, K.; Taniguchi, N.; Fukumoto, K. J. Am. Chem. Soc. 1992, 114, 4408-4410.; Ihara, M.; Taniguchi, T.; Makita, K.; Takano, M.; Ohnishi, M.; Taniguchi, N.; Fukumoto, K.; Kabuto, C. J. Am. Chem. Soc. 1993, 115, 8107-8115 and
17. (b) by tandem intramolecular Michael-aldol reactions: Ihara, M.; Ohnishi, M.; Takano, M.; Makita, K.; Taniguchi, N.; Fukumoto, K. J. Am. Chem. Soc. 1992, 114, 4408-4410.; Ihara, M.; Taniguchi, T.; Makita, K.; Takano, M.; Ohnishi, M.; Taniguchi, N.; Fukumoto, K.; Kabuto, C. J. Am. Chem. Soc. 1993, 115, 8107-8115 and
18. 3,6]octan-1-ylmethyl toluene-p-sulphonate: Luh, T-Y.; Lei, K. L. J. Chem. Soc., Chem. Commun. 1981, 214-215.
19. 1H NMR spectrum of the mixture of isomers.
20. 3) δ = 26.8 (d), 30.7 (t), 33.4 (t), 34.7 (d), 36.5 (d), 38.1 (t), 40.4 (t), 52.4 (d), 217.2 (s).
21. 3) δ = 20.9 (t), 27.5 (t), 30.5 (t), 31.0 (t), 31.5 (d), 34.2 (d), 35.0 (d), 37.8 (d), 41.6 (t).
22. 3) δ = 28.1 (t), 28.6 (d), 30.9 (t), 32.0 (t), 34.8 (d), 37.0 (d), 38.4 (t), 45.3 (d), 73.2 (d).
23. 3): δ = 34.3 (d), 35.9 (t, 2 C), 37.3 (d), 37.9 (d), 38.5 (d), 40.2 (t), 131.9 (d), 137.4 (d).