Strained polycycles by H5C5x free-radical cascades

Organic Letters

Volumn 8, Issue 6, 2006, Pages 1249-1251

  Moman, Edelmiro ^a   Nicoletti, Daniel ^a   Mouriño, Antonio ^a  

^a UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33646441436     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol060231w     Document Type: Article

References (39)

1. (a) Dhimane, A. L.; Aissa, C.; Malacria, M. Angew. Chem., Int. Ed. 2002, 41, 3284-3287.
2. (b) Aubert, C.; Courillon, C.; Dhimane, A. L.; Fensterbank, L.; Lacote, E.; Thorimbert, S.; Malacria, M. Curr. Opin. Drug Discov. Dev. 2002, 5, 928-936.
3. (c) Zard, S. Z. Radicals Reactions in Organic Synthesis; Oxford University Press: New York, 2003.
4. Pattenden, G.; Gonzalez, M. A.; McCulloch, S.; Walter, A.; Woodhead, S. J. Proc. Natl. Acad. Sci. 2004, 101, 12024-12029.
5. (a) Curran, D. P. Synthesis 1988, 417-439.
6. (b) Jarperse, C. P.; Curran, D. P.; Fevig, T. L. Chem. Rev. 1991, 91, 1237-1286.
7. (c) Beckwith, A. L. J. Chem. Soc. Rev. 1993, 22, 143-151.
8. Giese, B. In Radicals in Organic Synthesis; Renaud, P., Sibi, M. P., Eds.; Wiley-VCH: Weinheim, 2001; pp 381-399.
9. Activation and Functionalization of C-H Bonds; Goldberg, K. L, Goldman, A. S., Eds.; Oxford University Press: New York, 2004.
10. (a) Barton, D. H. R.; Beaton, J. M.; Geller, L. E.; Pechet, M. M. J. Am. Chem. Soc. 1960, 82, 2640-2641.
11. (b) Hartung, J.; Gottwald, T.; Ćpehar, K. Synthesis 2002, 11, 1469-1498.
12. Feray, L.; Kuznetsov, N.; Renaud, P. In Radicals in Organic Synthesis; Renaud, P., Sibi, M. P., Eds.; Wiley-VCH: Weinheim, 2001; pp 246-254.
13. (a) Čeković, Ž. Tetrahedron 2003, 59, 8073-8090.
14. (b) Čeković, Ž. J. Serb. Chem. Soc. 2005, 70, 287-318.
15. (a) Majetich, G. Tetrahedron 1995, 51, 7095-7129.
16. (b) Reese, P. B. Steroids 2001, 66, 481-497.
17. (c) Pellissier, H.; Santelli, M. Org. Prep. Proced. Int. 2001, 33, 455-476.
18. Čeković, Z.; Ilijev, D. Tetrahedron Lett. 1988, 29, 1441-1444.
19. To facilitate structural comparison, IUPAC-IUB steroid numbering is used: (a) Pure Appl. Chem. 1989, 61, 1783-1822.
20. (b) Eur. J. Biochem. 1989, 186, 429-458.
21. (c) Eur. J. Biochem. 1993, 213, 2.
22. (a) McCarroll, A. J.; Walton, J. C. Angew. Chem. Int. Ed. 2001. 40, 2224-2248.
23. (b) McCarroll, A. J.; Wallon, J. C. J. Chem. Soc., Perkin Trans, 1 2001, 3215-3229.
24. Zhang, W. Tetrahedron 2001, 57, 7237-7262.
25. de Armas, P.; Concepción, J. I.; Francisco, C. G.; Hernández, R.; Salazar, J. A.; Suárez, E. J. Chem. Soc., Perkin Trans, 1 1989, 405-411.
26. (a) Heusler, K.; Kalvoda, J. Angew. Chem., Int. Ed. 1964, 3, 525-538.
27. (b) Kalvoda, J.; Heusler, K. Synthesis 1971, 501-526.
28. Costa, S. C. P.; Miranda, M. J. S.; Sá e Melo, M. L.; Campos, A. S. Tetrahedron Lett. 1999, 40, 8711-8714.
29. 2: (0.24 g, 0.95 mmol) were added to deoxygenated 9:1 cyclohexane/benzene (50 mL). A solution of ester 3a (0.1 g, 0.36 mmol) in CyH (5 mL) was added. The reaction mixture was irradiated with a 500 W lamp for 130 min and concentrated to dryness. Zn powder (1.6 g, 24.47 mmol) was added to a solution of the residue in HOAc (30 mL), and this mixture was stirred for 16 h.
30. (a) Beckwith, A. L. J.; Schiesser, C. H. Tetrahedron Lett. 1985, 26, 373-376.
31. (b) Beckwith, A. L. J.; Schiesser, C. H. Tetrahedron 1985, 41, 3925-3941.
32. (c) Spellmeyer, D. C.; Houk, K. N. J. Org. Chem. 1987, 52, 959-974.
33. (d) Beckwith, A. L. J.; Zimmermann, J. J. Org. Chem. 1991, 56, 5791-5796.
34. Hartung, J. Eur. J. Org. Chem. 2001, 619-632.
35. Pasto, J.; Cottard, F. Tetrahedron Lett. 1994, 35, 4303-4306.
36. Refluxing in toluene also promotes the reaction (data not shown).
37. Typical procedure for the Barton-type reaction: 1a; a solution of sulfenate 3b (0.200 g, 0.46 mmol) in CyH (60 mL) was irradiated with a 300 W tungsten lamp for 60 min. After concentration, nickel Raney W-2 (0.5 g, 8.5 mmol, Fluka) was added to a solution of the residue (0.2 g) in anhydrous ethyl alcohol (20 mL), and this mixture was refluxed for 1 h.
38. Pennigton, L. D.; Overman, L. E. J. Org. Chem. 2003, 68, 7143-7157.
39. Varela, C.; Nilsson, K.; Torneiro, M.; Mouriño, A. Helv. Chim. Acta 2002, 85, 3251-3261.