Intramolecular anodic olefin coupling reactions: The construction of bridged bicyclic ring skeletons

Tetrahedron Letters

Volumn 39, Issue 44, 1998, Pages 8027-8030

  Reddy, S Hari Krishna ^a   Moeller, Kevin D ^a  

^a WASHINGTON UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BICYCLO[3.2.1]OCTANE DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL BINDING; CHEMICAL REACTION; CHEMICAL STRUCTURE;

EID: 0032578819     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01793-6     Document Type: Article

References (36)

1. 1. a. Hayashi, T.; Kishi, M.; Kawasaki, M.; Arisawa, M.; Shimizu, M.; Suzuki, S.; Yoshizaki, M.; Morita, N.; Tezuka, Y.; Kikuchi, T.; Berganza, L. H.; Ferro, E.; Basualdo, I. Tetrahedron Lett. 1987, 28, 3693.
2. b. Hayashi, T.; Kishi, M.; Kawasaki, M.; Arisawa, M.; Morita, N. J. Nat. Prod. 1988, 51, 360,
3. c. Hayashi, Y.; Okamura, K.; Kakemi, M.; Asano, S.: Mizutani, M.; Takeguchi, N.; Kawasaki, M.; Tezuka, Y.; Kikuchi, T.; Morita, N. Chem. Pharm. Bull. 1990, 38, 2740,
4. d. Asano, S.; Mizutani, M.; Hayashi, T.; Morita, N.; Takeguchi, N. J. Biol. Chem. 1990, 265, 22167,
5. e. Hayashi, K.; Niwayama, S.; Hayashi, T.; Nago, R.; Ochiai, H.; Morita, N. Antiviral Res. 1988, 9, 345,
6. f. Hayashi, K.; Hayashi, T.; Morita, N. Phytother. Res. 1992, 6, 6, and
7. g. Nishino, H.; Hayashi, T.; Arisawa, M.; Satomi, Y.; Iwashima, A. Oncology 1993, 50, 100.
8. 2. For previous syntheses of scopadulcic acid B see: a. Ziegler, F. E.; Wallace, O. B. J. Org. Chem. 1995, 60, 3626, and
9. b. Overman, L. E.; Ricca, D. J.; Tran, V.D. J. Am. Chem. Soc. 1993, 115, 2042. For other related synthetic efforts see:
10. c. Robichaud, A. J.; Meyers, A. I. J. Org. Chem. 1991, 56, 2607,
11. d. Abelman, M. M.; Overman, L. E. J. Am. Chem. Soc. 1988, 110, 2328, and
12. e. Kucera, D. J.; O'Connor, S. J.; Overman, L. E. J. Org. Chem. 1993, 58, 5304.
13. 3. For selected examples please see: a. Morehead, A. Jr.; Grubbs, R. J. Chem. Soc. Chem Commun. 1998, 265,
14. b. Delia, E. W.; Knill, A. M. J. Org. Chem. 1995, 60, 3518, and
15. c. Hadjiarapoglu, L.; de Meijere, A.; Seitz, H. -J.; Klein, I.: Spitzer, D. Tetrahedron Lett. 1994, 35, 3269 and references therein.
16. 3 oxidation of malonates a. O'Neil, S. V.; Quickley, C. A.; Snider, B. B. J. Org. Chem. 1997, 62, 1970,
17. b. Snider, B. B.; Merritt, J. E.; Dombroski, M. A.; Buckman, B. O. J. Org. Chem. 1991, 56, 5544, and
18. c. Snider, B. B.; Zhang, Q. Tetrahedron Lett. 1992, 33, 5921, as well as the electrochemical version of an arene-olefination reaction
19. d. Maki, S.; Toyoda, K.; Kosemura, S; Yamamura, S. Chem Lett. 1993, 1059,
20. e. Maki, S.; Asaba, N.; Kosemura, S.; Yamamura, S.; Tetrahedron Lett. 1992, 33, 4169, and
21. f. Shiuri, Y.; Okimo, Y.; Shigemori, H.; Yamamura, S. Tetrahedron Lett. 1987, 28, 6661.
22. 5. For a general list of references concerning oxidative cyclization reactions see Moeller, K. D. Topics in Current Chemistry 1997, 185, 49 and reference 3 therein. For a pair of very recent examples see: a. Jahn, U.; Hartmann, P. J. Chem. Soc Chem. Commun. 1998 209 and
23. 5. For a general list of references concerning oxidative cyclization reactions see Moeller, K. D. Topics in Current Chemistry 1997, 185, 49 and reference 3 therein. For a pair of very recent examples see: a. Jahn, U.; Hartmann, P. J. Chem. Soc Chem. Commun. 1998 209 and
24. b. Ryter, K.; Livinghouse, T. J. Am. Chem. Soc. 1998, 120, 2658.
25. 6. For selected references see: a. Frey D. A.; Marx, J. A.; Moeller, K. D. Electrochimica Acta, 1997, 42, 1967,
26. b, New, D. G.; Tesfai, Z.; Moeller, K. D. J. Org. Chem. 1996, 61, 1578,
27. c. Hudson, C. M.; Moeller, K. D. J. Am. Chem. Soc. 1994. 59, 2381,
28. d. Moeller, K. D.; Tinao, L. V. J. Am. Chem. Soc. 1992, 114, 1033, and
29. e. Hudson, C. M.; Marzabadi, M. R.; Moeller, K. D.; New, D. G. J. Am. Chem. Soc. 1991, 113, 7372.
30. 7. Tinao-Wooldridge, L. V.; Moeller, K. D.; Hudson, C. M. J. Org. Chem. 1994, 59, 2381.
31. 8. a. Little, R. D.; Wolin, R. L.; Sowell, C. G. J. Electrochem. Soc. Jpn. (Denki Kagaku) 1994, 62, 1105, and
32. b. Sowell, C. G.; Wolin, R. L.; Little, R. D. Tetrahedron Lett. 1990, 31, 485.
33. 9. Both substrates were synthesized from 3-allylcyclopentane. For 7 the olefin was hydroborated, the resulting alcohol converted to an aldehyde, and then both carbonyls converted into enol ethers with the use of a Wittig reaction. The procedure for 9 was the same except the olefin of the starting material was cleaved using an ozonolysis reaction in order to make a keto-aldehyde with one less carbon in the chain.
34. 10. Preparative electrolyses were conducted utilizing a Model 630 couloineter, a Model 410 potentiostatic controller, and a Model 420A power supply purchased from The Electrosynthesis Co., Inc.
35. 11. Frey, D. A.; Wu, N.; Moeller, K. D. Tetrahedron Lett. 1996, 37, 8317.
36. 12. All CV data was measured using a BAS 100B Electrochemical Analyzer, Pt working and auxiliary electrodes, a Ag/AgCl reference electrode, a 0.1 M LiCIO4 in acetonitrile electrolyte solution, a substrate concentration of 0.025 M. and a sweep rate of 25 mV/sec. The MeOH/THF solvent used in the preparative studies and the presence of 2,6-lutidine were avoided because they complicated the voltammograms. The relevance of the data reported to the preparative experiments was checked by measuring the Ep/2 value for substrate 7 under both sets of conditions. No difference was observed.