Diastereoselective triple radical cyclization of a bromomethyldimethylsilyl allyl ether

Tetrahedron Letters

Volumn 37, Issue 35, 1996, Pages 6295-6298

  Kende, Andrew S ^a   Journet, Michel ^a,b   Ball, Richard G ^b   Tsou, Nancy N ^b  

^a UNIVERSITY OF ROCHESTER   (United States)

^b MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

POLYCYCLIC AROMATIC COMPOUND;

ARTICLE; CYCLIZATION; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030603047     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01383-4     Document Type: Article

References (15)

1. (1) a) Holton, R. A.; Somoza, C.; Kim, H.-B.; Liang, F.; Biediger, R. J.; Boatman, P. D.; Shindo, M.; Smith, C. C.; Kim, S.; Nadizadeh, H.; Suzuki, Y.; Tao, C.; Vu, P.; Tang, S.; Zhang, P.; Murthi, K. K.; Gentile, L. N.; Liu, J. H. J. Am. Chem. Soc. 1994, 116, 1597-1598;
2. b) Holton, R. A.; Kim, H.-B.; Somoza, C.; Liang, F.; Biediger, R. J.; Boatman, P. D.; Shindo, M.; Smith, C. C.; Kim, S.; Nadizadeh, H.; Suzuki, Y.; Tao, C.; Vu, P.; Tang, S.; Zhang, P.; Murthi, K. K.; Gentile, L. N.; Liu, J. H ibid. 1994, 116, 1599-1600;
3. c) Nicolaou, K. C.; Yang, Z.; Liu, J. J.; Ueno, H.; Nantermet, P. G.; Guy, R. K.; Claiborne, C. F.; Renaud, J.; Couladouros, E. A.; Paulvannan, K.; Sorensen, E. J. Nature 1994, 367, 630-635;
4. d) Masters, J. J.; Link, J. T.; Snyder, L. B.; Young, W. B.; Danishefsky, S. J. Angew. Chem. Int. Ed. Engl. 1995, 34, 1723-1726.
5. (2) Kende, A. S.; Johnson, S.; Sanfilippo, P.; Hodges, J. C.; Jungheim, L. N. J. Am. Chem. Soc. 1986, 108, 3513-3515.
6. (3) 8-membered rings have been previously synthesized via 8-endo-trig radical cyclizations. Lee, E.; Yoon, C. H.; Lee, T. H. J. Am. Chem. Soc. 1992, 114, 10981-10983.
7. (4) Curran, D. P. Radical Addition Reactions and Radical Cyclizations and Sequential Radical Reactions. In Comprehensive Organic Synthesis; Trost, B.M., Fleming I., Eds.; Pergamon: New York, 1992; Vol. 4, pp 715-831.
8. (5) a) Stork, G.; Kahn, M. J. Am. Chem. Soc. 1985, 107, 500-501;
9. b) Nishiyama, N.; Kitajama, T.; Matsumoto, M.; Itoh, K. J. Org. Chem. 1984, 49, 2298-2300.
10. (6) Trost, B. M.; Molander, G. A. J. Am. Chem. Soc. 1981, 103, 5969-5672.
11. (7) Hitchcock, S. A.; Pattenden, G. Tetrahedron Lett. 1992, 33, 4843-4846.
12. +) 421.2590, measured, 421.2603.
13. (9) Relative stereochemistry in 12a and 12b was unambiguously established by X-ray crystallography of each diol after having been recrystallized from nitromethane. Atomic coordinates for 12a and 12b can be obtained on request from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK. (equation presented)
14. (10) It is known that steric influences do not depend on the steric hindrance of the alkyl centered radical but depend strongly on the position of the shielding group of the alkene. For example, it has been reported that the rate of the addition of a cyclohexyl radical on an α-t-butyl-substituted acrylate was reduced by a factor of approximatively 3000 vs. the unsubstituted acrylate: Giese, B.; Lachhein, S. Angew. Chem. Int. Ed. Engl. 1981, 20, 967-967.
15. (11) We are grateful to Glaxo Research Institute (USA) for partial support of this research.