Asymmetric synthesis of actinoidic acid derivatives

Organic Letters

Volumn 2, Issue 16, 2000, Pages 2459-2462

  Boisnard, Sabine ^a   Neuville, Luc ^a   Bois Choussy, Michèle ^a   Zhu, Jieping ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

BIPHENYL DERIVATIVE; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; PHENYLACETIC ACID DERIVATIVE; VANCOMYCIN;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; SYNTHESIS;

BIPHENYL COMPOUNDS; INDICATORS AND REAGENTS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; PHENYLACETATES; VANCOMYCIN;

EID: 0034632401     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006110s     Document Type: Article

References (37)

1. (a) Williams, D. H.; Bardsley, B. Angew. Chem., Int. Ed. 1999, 38, 1173-1193.
2. (b) Zhu, J. Exp. Opin. Ther. Pat. 1999, 9, 1005-1019.
3. (a) Zhu, J. Synlett 1997, 133-144.
4. (b) Nicolaou, K. C.; Boddy, C. N. C.; Bräse, S.; Winssinger, N. Angew. Chem., Int. Ed. 1999, 38, 2096-2152.
5. (a) Evans, D. A.; Wood, M. R.; Trotter, B. W.; Richardson, T. I.; Barrow, J. C.; Katz, J. L. Angew. Chem., Int. Ed. 1998, 37, 2700-2704; 2704-2708.
6. (b) Nicolaou, K. C.; Natarajan, S.; Li, H.; Jain, N. F.; Hughes, R.; Solomon, M. E.; Ramanjulu, J. M.; Boddy, C. N. C.; Takayanagi, M. Angew. Chem., Int. Ed. 1998, 37, 2708-2714; 2714-2716; 2717-2719.
7. (c) Boger, D. L.; Miyazaki, S.; Kim, S. H.; Wu, J. H.; Loiseleur, O.; Castle, S. L. J. Am. Chem. Soc. 1999, 121, 3226-3227.
8. (d) For total synthesis of vancomycin, see: Nicolaou, K. C.; Mitchell, H. J.; Jain, N. F.; Winssinger, N.; Hughes, R.; Bando, T. Angew. Chem., Int. Ed. 1999, 38, 240-244.
9. Neuville, L.; M. Bois-Choussy, Zhu, J. Tetrahedron Lett. 2000, 41, 1747-1751.
10. (a) Rama Rao, A. V.; Chakraborty, T. K.; Joshi, S. P. Tetrahedron Lett. 1992, 33, 4045-4048.
11. (b) Rama Rao, A. V. Reddy, K. L.; Reddy, M. M. Tetrahedron Lett. 1994, 35, 5039-5042.
12. Evans, D. A.; Ecrard, D. A.; Rychnovsky, S. D.; Fruh, T.; Whittingham, W. G.; DeVries, K. M. Tetrahedron Lett. 1992, 33, 1189-1192.
13. Lipshutz, B. H.; Peter Müller, P.; Leinweber, D. Tetrahedron Lett. 1999, 40, 3677-3680.
14. (a) Miyano, S.; Tobita, M.; Hashimoto, H. Bull. Chem. Soc. Jpn. 1981, 54, 3522-3526.
15. (b) Meyers, A. I.; Lutomski, K. A. J. Am. Chem. Soc. 1982, 104, 879-881.
16. (c) Wilson, J. M.; Cram, D. J. J. Am. Chem. Soc. 1982, 104, 881-884.
17. (d) Yamamoto, K.; Fukushima, H.; Nakazaki, M. J. Chem. Soc., Chem. Commun. 1984, 1490-1491.
18. (e) Hayashi, T.; Hayashizaki, K.; Kiyoi, T.; Ito, Y. j. Am. Chem. Soc. 1988, 110, 8153-8156.
19. (f) Osa, T.; Kashiwagi, Y.; Yanagisawa, Y.; Bobbitt, J. M. J. J. Chem. Soc., Chem. Commun. 1994, 2535-2537.
20. Zhu, J.; Beugelmans, R.; Bigot, A.; Singh, G. P.; Bois-Choussy, M. Tetrahedron Lett. 1993, 34, 7401-7404.
21. (a) Rueman, M.; Meyers, A. I. Tetrahedron 1985, 41, 837-860.
22. (b) Gant, T. G.; Meyers, A. I. Tetrahedron 1994, 50, 2297-2360;
23. For the protection of carboxylic acid as oxazoline, see: Meyers, A. I.; Gabel, R.; Mihelich, E. D. J. Org. Chem. 1978, 43, 1372-1379.
24. (b) Degnan, A. P.; Meyers, A. I. J. Am. Chem. Soc. 1999, 121, 2762-2769.
25. Frump, J. A. Chem. Rev. 1971, 71, 483-505.
26. Lai, Y. H. Synthesis 1981, 585-604.
27. No experiment has been caried out to determine the energy barrier for interconversion of two atropisomers. The aryl-aryl bond rotation in compound 14 might be an easy process according to Meyers: Meyers, A. I.; Flisak, J. R.; Aitken, R. A. J. Am. Chem. Soc. 1987, 109, 5446-5452.
28. Feuer, H.; Bevinakatti, S. H.; Luo, X. G. J. Heterocycl. Chem. 1987, 24, 9-13.
29. Wilson, S. R.; Mao, D. T.; Khatri, H. N. Synth. Commun. 1980, 10, 17-23.
30. Vergne, C.; Bouillon, J. P.; Chastanet, J. Bois-Choussy, M.; Zhu, J. Tetrahedron: Asymmetry 1998, 9, 3095-3103.
31. Davis, F. A.; Zhou, P.; Chen, B. C. Chem. Soc. Rev. 1998, 27, 13-18.
32. (a) Davis, F. A.; Zhang, Y.; Andemichael, Y.; Fang, T.; Fanelli, D. L.; Zhang, H. J. Org. Chem. 1999, 64, 1403-1406.
33. (b) Liu, G.; Cogan, D. A.; Ellman, J. A.; J. Am. Chem. Soc. 1997, 119, 9913-9914.
34. Davis, F. A.; Fanelli, D. L. J. Org. Chem. 1998, 63, 1981-1985.
35. The oxoammonium salt mediated oxidation (Tempo-NaClO) gave ring chlorinated acid in 95% yield. Modification of reaction conditions failed to avoid this undesired chlorinination reaction, cf. ref 4.
36. Experimental evidences suggested that epimerization occurred at the A ring unit via possibly the amino aldehyde intermediate which has been isolated and proved to be stereochemically unstable.
37. Jeffs, P. W.; Chan, G.; Mueller, L.; DeBrosse, C.; Webb, L.; Sitrin, R. J. Org. Chem. 1986, 57, 4272-4278.