Intermolecular reductive cyclodimerization of cyclic α,β- unsaturated ketones promoted by a low-valent titanium reagent: A facile synthesis of some new spiro compounds

Synthesis

Volumn , Issue 12, 2007, Pages 1797-1806

  Shi, Da Qing ^a,b   Dou, Guo Lan ^b   Li, Zheng Yi ^b   Shi, Chun Ling ^b   Li, Xiao Yue ^b   Jiang, Hong ^c   Ni, Sai Nan ^b   Ji, Shun Jun ^a  

^a SOOCHOW UNIVERSITY   (China)

^b JIANGSU NORMAL UNIVERSITY   (China)

^c JIANGSU NORMAL UNIVERSITY   (China)

Author keywords

Cyclic , unsaturated ketones; Low valent titanium; Spiro compounds; Stereochemistry

Indexed keywords

INTERMOLECULAR REDUCTIVE CYCLODIMERIZATION; LOW-VALENT TITANIUM; TITANIUM REAGENT; UNSATURATED KETONES;

CYCLIZATION; KETONES; STEREOCHEMISTRY; X RAY DIFFRACTION ANALYSIS;

UNSATURATED COMPOUNDS;

1,2 BIS (4 FLUOROPHENYL) 3A HYDROXY 1,3A,8,8A TETRAHYDRO 2H SPIRO[CYCLOPENT[A]INDENE 3,2' INDEN] 1'(3'H) ONE; 1,2 BIS(1,3 BENZODIOXOL 5 YL) 3A HYDROXY 1,3A,8,8A TETRAHYDRO 2H SPIRO[CYCLOPENT[A]INDENE 3,2' INDEN] 1'(3'H) ONE; 1,2 BIS(2 FURYL) 3A HYDROXYL 1,3A,8,8A TETRAHYDRO 2H SPIRO[CYCLOPENT[A]INDENE 3,2' INDEN] 1'(3'H) ONE; 1,2 BIS(3 CHLOROPHENYL) 3A HYDROXY 1,3A,8,8A TETRAHYDRO 2H SPIRO[CYCLOPENT[A]INDENE 3,2' INDEN] 1'(3'H) ONE; 1,2 BIS(3,4 DICHLOROPHENYL) 3A HYDROXY 1,3A,8,8A TETRAHYDRO 2H SPIRO[CYCLOPENT[A]INDENE 3,2' INDEN] 1'(3'H) ONE; 1,2 BIS(3,4 DIMETHYLPHENYL) 3A HYDROXY 1,3A,8,8A TETRAHYDRO 2H SPIRO[CYCLOPENT[A]INDENE 3,2' INDEN] 1'(3'H) ONE; 1,2 BIS(4 BROMOPHENYL) 3A HYDROXY 1,3A,8,8A TETRAHYDRO 2H SPIRO[CYCLOPENT[A]INDENE 3,2' INDEN] 1'(3'H) ONE; 1,2 BIS(4 CHLOROPHENYL) 3A HYDROXY 1,3A,8,8A TETRAHYDRO 2H SPIRO[CYCLOPENT[A]INDENE 3,2' INDEN] 1'(3'H) ONE; 2 BENZYLIDENE 1 TETRALONE; 2 BENZYLIDENEINDAN 1 ONE; 2,3 BIS (4 FLUOROPHENYL) 3,3',3A 4,4',5 HEXAHYDRO 1'H SPIRO[CYCLOPENT[A]NAPHTHALENE 1,2' NAPHTHALENE] 1',9B(2H) DIOL; 2,3 BIS(1,3 BENZODIOXOL 5 YL) 3,3',3A,4,4',5 HEXAHYDRO 1'H SPIRO[CYCLOPENT[A]NAPHTHALENE] 1',9B(2H) DIOL; 2,3 BIS(2,4 DICHLORPHENYL) 3,3',3A,4,4',5 HEXAHYDRO 1'H SPIRO[CYCLOPENT[A]NAPHTHALENE 1,2' NAPHTHALENE] 1',9B(2H) DIOL; 2,3 BIS(3,4 DICHLOROPHENYL) 3,3',3A,4,4',5 HEXAHYDRO 1'H SPIRO[CYCLOPENT[A]NAPHTHALENE 1,2' NAPHTHALENE] 1',9B(2H) DIOL; 2,3 BIS(3,4 DIMETHOXYPHENYL) 3,3',3A,4,4',5 HEXAHYDRO 1'H SPIRO[CYCLOPENT[A]NAPHTHALENE 1,2' NAPHTHALENE] 1',9B(2H) DIOL; 2,3 BIS(3,4 DIMETHYLPHENYL) 3,3',3A,4,4',5 HEXAHYDRO 1'H SPIRO[CYCLOPENT[A]NAPHTHALENE 1,2' NAPHTHALENE] 1',9B(2H)DIOL; 2,3 BIS(4 BROMOPHENYL) 3,3',3A,4,4',5 HEXAHYDRO 1'H SPIRO[CYCLOPENT[A]NAPHTHALENE 1,2' NAPHTHALENE] 1',9B(2H) DIOL; 2,3 DI(4 TOLYL) 3,3',3A,4,4',5 HEXAHYDRO 1'H SPIRO[CYCLOPENT[A]NAPHTHALENE 1,2' NAPHTHALENE 1',9B(2H) DIOL; 2,3 DIPHENYL 3,3',3A,4,4',5 HEXAHYDRO 1'H SPIRO[CYCLOPNET[A]NAPHTHALENE 1,2' NAPTHALENE] 1',9B(2H) DIOL; 3 BENZYLIDENECHROMAN 4 ONE; 3 BENZYLIDENETHIOCHROMAN 4 ONE; 3A HYDROXY 1,2 BIS(2 THIOFURYL) 1,3A,8,8A TETRAHYDRO 2H SPIRO[CYCLOPENT[A]INDENE 3,2' INDEN] 1'(3'H) ONE; 3A HYDROXY 1,2 BIS(4 METHOXYPHENYL) 1,3A,8,8A TETRAHYDRO 2H SPIRO[CYCLOPENT[A]INDENE 3,2' INDEN] 1'(3'H) ONE; 3A HYDROXY 1,2 BIS(4 TOLYL) 1,3A,8,8A TETRAHYDRO 2H SPIRO[CYCLOPENT[A]INDENE 3,2' INDEN] 1'(3'H) ONE; 9B' HYDROXY 2',3' DI(4 TOLYL) 2',3',3A',9B' TETRAHYDRO 4H,4'H SPIRO[CHROMENE 3,1' CYCLOPENTA[C]CHROMENE] 4 ONE; BIS(4 FLUOROPHENYL) 9B' HYDROXY 2',3',3A',9B' TETRAHYDRO 4H,4'H SPIRO[CHROMENE 3,1' CYCLOPENTA[C]CHROMEN] 4 ONE; KETONE DERIVATIVE; SPIRO COMPOUND; TITANIUM; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ARTICLE; BIOLOGICAL ACTIVITY; CHEMICAL REACTION; DIMERIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; PROTON NUCLEAR MAGNETIC RESONANCE; PROTON TRANSPORT; RACEMIZATION; STEREOCHEMISTRY; X RAY DIFFRACTION;

EID: 34347394565     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-983707     Document Type: Article

References (41)

1. McMurry, J. E. Chem. Rev. 1989, 89, 1513.
2. (a) McMurry, J. E.; Fleming, M. P. J. Org. Chem. 1976, 41, 896.
3. (b) McMurry, J. E. Acc. Chem. Res. 1983, 16, 405.
4. (c) Lenoir, D. Synthesis 1989, 883.
5. (d) Furstner, A.; Bogdanovi, B. Angew. Chem., Int. Ed. Engl. 1996, 35, 2443.
6. (e) Mariappan, P.; Mallad, P. R.; Kanth, J. V. B. Tetrahedron Lett. 1996, 37, 4767.
7. (f) Mariappan, P.; Gadthula, S.; Surisetti, S. Tetrahedron Lett. 2001, 42, 7123.
8. (g) McMurry, J. E.; Dushin, R. G. J. Am. Chem. Soc. 1990, 112, 6942.
9. (a) Shi, D. Q.; Chen, J. X.; Chai, W. Y.; Chen, W. X.; Kao, T. Y. Tetrahedron Lett. 1993, 34, 2963.
10. (b) Shi, D. Q.; Rong, L. C.; Wang, J. X.; Zhuang, Q. Y.; Wang, X. S.; Hu, H. W. Tetrahedron Lett. 2003, 44, 3199.
11. (c) Shi, D. Q.; Wang, J. X.; Shi, C. L.; Rong, L. C.; Zhuang, Q. Y.; Hu, H. W. Synlett 2004, 1098.
12. (d) Shi, D. Q.; Shi, C. L.; Wang, X. S.; Zhuang, Q. Y.; Tu, S. J.; Hu, H. W. Synlett 2004, 2239.
13. (a) Li, J.; Shi, D. Q.; Chen, W. X. Heterocycles 1997, 45, 2381.
14. (b) Shi, D. Q.; Lu, Z. S.; Mu, L. L.; Dai, G. Y. Synth. Commun. 1997, 27, 4121.
15. (c) Zhou, L. H.; Tu, S. J.; Shi, D. Q.; Dai, G. Y. J. Chem. Res., Synop. 1998, 398.
16. (d) Zhou, L. H.; Tu, S. J.; Shi, D. Q.; Chen, W. X. Synthesis 1998, 851.
17. (e) Shi, D. Q.; Rong, L. C.; Shi, C. L.; Zhuang, Q. Y.; Wang, X. S.; Tu, S. J.; Hu, H. W. Synthesis 2005, 717.
18. (a) Davon, T. K.; Scott, A. I. Handbook of Naturally Occurring Compounds, Vol. II.; Academic Press: New York, 1972.
19. (b) Fraga, B. M. Nat. Prod. Rep. 1993, 10, 397.
20. (c) Heathcock, C. H.; Graham, S. L.; Pirrung, M. C.; Plavac, F.; White, C. T. The Total Synthesis of Natural Products, Vol. 5; Wiley-Interscience: New York, 1983, 264.
21. Brook, C. J. W.; Watson, D. G. Nat. Prod. Rep. 1985, 2, 427.
22. Bozan, B.; Ozek, T.; Kurkcuoglu, M.; Kirimer, N.; Baser, K.; Husnu, C. Planta Med. 1999, 65, 781.
23. (a) Tanis, S. P.; Herrinton, P. M.; Dixon, L. A. Tetrahedron Lett. 1985, 26, 5347.
24. (b) Posner, G. H.; Hamill, T. G. J. Org. Chem. 1988, 53, 6031.
25. (c) Haack, R. A.; Beck, K. R. Tetrahedron Lett. 1989, 30, 1605.
26. (d) Imanishi, T.; Ohra, T.; Sugiyama, K.; Veda, Y.; Takemoto, Y.; Iwata, C. J. Chem. Soc., Chem. Commun. 1992, 269.
27. (e) Kuroda, C.; Hirono, Y. Tetrahedron Lett. 1994, 35, 6895.
28. (f) Oesterreich, K.; Spitzner, D. Tetrahedron 2002, 58, 4331.
29. (g) Kuroda, C.; Koshio, H.; Koito, A.; Sumiya, H.; Murase, A.; Hirono, Y. Tetrahedron 2004, 56, 6441.
30. Tataki, K.; Beppu, F.; Tanaka, S.; Tsubaki, Y.; Jintoku, Y.; Fujiwara, Y. J. Chem. Soc., Chem. Commun. 1990, 516.
31. Bao, J.; Bei, M.; Lu, J.; Zhang, J.; Song, Q. Chin. Chem. Lett. 1993, 4, 593.
32. Enholm, E. J.; Kinter, K. S. J. Org. Chem. 1995, 60, 4850.
33. Zhou, L. H.; Shi, D. Q.; Gao, Y.; Shen, W. B.; Dai, G. Y.; Chen, W. X. Tetrahedron Lett. 1997, 38, 2729.
34. Cabrera, A.; Le Lagadec, R.; Sharma, P.; Arias, J. L.; Toscano, R. A.; Velasco, L.; Gavino, R.; Alvarez, C.; Salmon, M. J. Chem. Soc., Perkin Trans. 1 1998, 3609.
35. (a) Fournier, F.; Berthelot, J.; Basselier, J. J. Tetrahedron 1985, 41, 5667.
36. (b) Kise, N.; Kitagishi, Y.; Ueda, N. J. Org. Chem. 2004, 69, 959.
37. Li, Z. Y.; Shi, D. Q.; Shi, C. L.; Dou, G. L. Acta Crystallogr., Sect. E 2005, 61, o2709.
38. Shi, D. Q.; Shi, C. L.; Wang, X. S.; Rong, L. C.; Hu, H. W. Acta Crystallogr., Sect. E 2004, 60, o1859.
39. -1. Intensity data were collected on a Smart-1000 diffractometer with graphite monochromated Mo Kα radiation (λ = 0.71073 Å) using the ω scan mode with 2.04° < 6 θ 25.01°; 4637 unique reflections were measured and 1921 reflections with I > 2σ(I) were used in the Fourier techniques. The final refinement was converged to R = 0.0570 and wR = 0.1140.
40. -1. Intensity data were collected on a Smart-1000 diffractometer with graphite monochromated Mo Kα radiation (λ = 0.71073 Å) using the ω scan mode with 1.93° < θ < 25.01°; 5625 unique reflections were measured and 2927 reflections with I > 2σ(I) were used in the Fourier techniques. The final refinement was converged to R = 0.0500 and wR = 0.1026.
41. Bell, V. L.; Cromwell, N. H. J. Org. Chem. 1958, 23, 789.