Enantioselective synthesis of the Prelog-Djerassi lactonic acid via group-selective aldolization/desymmetrization of a meso dialdehyde with a chiral N-propionylsultam

Tetrahedron Letters

Volumn 38, Issue 5, 1997, Pages 809-812

  Oppolzer, Wolfgang ^a   Walther, Eric ^a   Balado, Carlos Pérez ^a   De Brabander, Jef ^a  

^a UNIVERSITY OF GENEVA   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

LACTONE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0031028094     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02408-2     Document Type: Article

References (35)

1. a) R. W. Hoffmann. Angew. Chem. 1987, 99, 503; Angew. Chem. Int. Ed. Engl. 1987, 26, 489;
2. a) R. W. Hoffmann. Angew. Chem. 1987, 99, 503; Angew. Chem. Int. Ed. Engl. 1987, 26, 489;
3. b) R. W. Hoffmann, G. Dahmann, M. W. Andersen, Synthesis 1994, 629 and references cited therein;
4. c) D. A. Evans, A. M. Ratz, B. E. Huff, G. S. Sheppard, J. Am. Chem. Soc. 1995, 117, 3448 and references cited therein;
5. a) Reviews: C. H. Heathcock in 'Asymmetric Synthesis' Ed. J. D. Morrison, Academic Press 1984, Vol 3, p.111; C. H. Heathcock in 'Comprehensive Organic Synthesis' Ed. B. M. Trost, I. Fleming, Pergamon 1991, Vol 2, p. 181; B. M. Kim, S. F. Williams, S. Masamune, ibid., p. 239; A. S. Franklin, I. Paterson, Contemporary Organic Synthesis 1994, 317;
6. a) Reviews: C. H. Heathcock in 'Asymmetric Synthesis' Ed. J. D. Morrison, Academic Press 1984, Vol 3, p.111; C. H. Heathcock in 'Comprehensive Organic Synthesis' Ed. B. M. Trost, I. Fleming, Pergamon 1991, Vol 2, p. 181; B. M. Kim, S. F. Williams, S. Masamune, ibid., p. 239; A. S. Franklin, I. Paterson, Contemporary Organic Synthesis 1994, 317;
7. a) Reviews: C. H. Heathcock in 'Asymmetric Synthesis' Ed. J. D. Morrison, Academic Press 1984, Vol 3, p.111; C. H. Heathcock in 'Comprehensive Organic Synthesis' Ed. B. M. Trost, I. Fleming, Pergamon 1991, Vol 2, p. 181; B. M. Kim, S. F. Williams, S. Masamune, ibid., p. 239; A. S. Franklin, I. Paterson, Contemporary Organic Synthesis 1994, 317;
8. a) Reviews: C. H. Heathcock in 'Asymmetric Synthesis' Ed. J. D. Morrison, Academic Press 1984, Vol 3, p.111; C. H. Heathcock in 'Comprehensive Organic Synthesis' Ed. B. M. Trost, I. Fleming, Pergamon 1991, Vol 2, p. 181; B. M. Kim, S. F. Williams, S. Masamune, ibid., p. 239; A. S. Franklin, I. Paterson, Contemporary Organic Synthesis 1994, 317;
9. b) double Stereodifferentiation: W. R. Roush, J. Org. Chem. 1991, 56, 4151; D. A. Evans, H. P. Ng, D. L. Rieger, J. Am. Chem. Soc. 1993, 115, 11446; D. A. Evans, M. J. Dart, J. L. Duffy, D. L. Rieger, J. Am. Chem. Soc. 1995, 117, 9073.
10. b) double Stereodifferentiation: W. R. Roush, J. Org. Chem. 1991, 56, 4151; D. A. Evans, H. P. Ng, D. L. Rieger, J. Am. Chem. Soc. 1993, 115, 11446; D. A. Evans, M. J. Dart, J. L. Duffy, D. L. Rieger, J. Am. Chem. Soc. 1995, 117, 9073.
11. b) double Stereodifferentiation: W. R. Roush, J. Org. Chem. 1991, 56, 4151; D. A. Evans, H. P. Ng, D. L. Rieger, J. Am. Chem. Soc. 1993, 115, 11446; D. A. Evans, M. J. Dart, J. L. Duffy, D. L. Rieger, J. Am. Chem. Soc. 1995, 117, 9073.
12. a) W. Oppolzer, J. Blagg, I. Rodriguez, E. Walther, J. Am. Chem. Soc. 1990, 112, 2767;
13. b) W. Oppolzer, I. Rodriguez, C. Starkemann, E. Walther, Tetrahedron Lett. 1990, 31, 5019;
14. c) W. Oppolzer, C. Starkemann, I. Rodriguez, G. Bernardinelli, ibid. 1991, 32, 61;
15. d) W. Oppolzer, P. Lienard, ibid. 1993, 34, 4321;
16. e) W. Oppolzer, I. Rodriguez, Helv. Chim. Acta 1993, 76, 1275.
17. W. Oppolzer, J. De Brabander, E. Walther, G. Bernardinelli, Tetrahedron Lett. 1995, 36, 4413.
18. a) Reviews dealing with chain desymmetrizations: C. S. Poss, S. L. Schreiber, Acc. Chem. Res. 1994, 27, 9; S. R. Magnuson, Tetrahedron 1995, 51, 2167;
19. a) Reviews dealing with chain desymmetrizations: C. S. Poss, S. L. Schreiber, Acc. Chem. Res. 1994, 27, 9; S. R. Magnuson, Tetrahedron 1995, 51, 2167;
20. b) For an elegant approach towards the synthesis of polypropionate fragments via a kinetic desymmetrization of polycyclic systems see: C. Marchionni, P. Vogel, P. Roversi, Tetrahedron Lett. 1996, 37, 4149.
21. a) C. Djerassi, J. A. Zderic, J. Am. Chem. Soc. 1956, 78, 6390;
22. b) R. Anliker, D. Dvomik, K. Gubler, H. Heusser, V. Prelog, Helv. Chim. Acta 1956, 39, 1785.
23. R. W. Rickards, R. M. Smith, Tetrahedron Lett. 1970, 11, 1025; D. G. Manwaring, R. W. Rickards, R. M. Smith, ibid. 1970, 11, 1029.
24. R. W. Rickards, R. M. Smith, Tetrahedron Lett. 1970, 11, 1025; D. G. Manwaring, R. W. Rickards, R. M. Smith, ibid. 1970, 11, 1029.
25. a) For a review dealing with the synthesis of the Prelog-Djerassi lactonic acid see: S. F. Martin, D. E. Guinn, Synthesis 1991, 245;
26. b) more recent syntheses: M. Miyashita, M. Hoshino, A. Yoshikoshi, K. Kawamine, K. Yoshihara, H. Irie, Chem. Lett. 1992, 1101; N. Ouvrard, J. Rodriguez, M. Santelli, Tetrahedron Lett. 1993, 34, 1149; C. Santelli-Rouvier, S. Lefrere, M. Santelli, ibid. 1994, 35, 6101; N. Ouvrard, J. Rodriguez, M. Santelli, Nat. Prod. Lett. 1994, 5, 153.
27. b) more recent syntheses: M. Miyashita, M. Hoshino, A. Yoshikoshi, K. Kawamine, K. Yoshihara, H. Irie, Chem. Lett. 1992, 1101; N. Ouvrard, J. Rodriguez, M. Santelli, Tetrahedron Lett. 1993, 34, 1149; C. Santelli-Rouvier, S. Lefrere, M. Santelli, ibid. 1994, 35, 6101; N. Ouvrard, J. Rodriguez, M. Santelli, Nat. Prod. Lett. 1994, 5, 153.
28. b) more recent syntheses: M. Miyashita, M. Hoshino, A. Yoshikoshi, K. Kawamine, K. Yoshihara, H. Irie, Chem. Lett. 1992, 1101; N. Ouvrard, J. Rodriguez, M. Santelli, Tetrahedron Lett. 1993, 34, 1149; C. Santelli-Rouvier, S. Lefrere, M. Santelli, ibid. 1994, 35, 6101; N. Ouvrard, J. Rodriguez, M. Santelli, Nat. Prod. Lett. 1994, 5, 153.
29. b) more recent syntheses: M. Miyashita, M. Hoshino, A. Yoshikoshi, K. Kawamine, K. Yoshihara, H. Irie, Chem. Lett. 1992, 1101; N. Ouvrard, J. Rodriguez, M. Santelli, Tetrahedron Lett. 1993, 34, 1149; C. Santelli-Rouvier, S. Lefrere, M. Santelli, ibid. 1994, 35, 6101; N. Ouvrard, J. Rodriguez, M. Santelli, Nat. Prod. Lett. 1994, 5, 153.
30. D. A. Evans, J. V. Nelson, E. Vogel, T. R. Taber, J. Am. Chem. Soc. 1981, 103, 3099.
31. Meso dialdehyde 5 was prepared from the corresponding known diol (J. C. Anderson, S. V. Ley, S. P. Marsden, Tetrahedron Lett. 1994, 35, 2087; Y.-F. Wang, C.-S. Chen, G. Girdaukas, C. J. Sih, J. Am. Chem. Soc. 1984, 106, 3695 ) via double Swern oxidation followed by a non-aqueous workup (precipitation of the ammoniumsalts with toluene and hexane and filtration over celite).
32. Meso dialdehyde 5 was prepared from the corresponding known diol (J. C. Anderson, S. V. Ley, S. P. Marsden, Tetrahedron Lett. 1994, 35, 2087; Y.-F. Wang, C.-S. Chen, G. Girdaukas, C. J. Sih, J. Am. Chem. Soc. 1984, 106, 3695 ) via double Swern oxidation followed by a non-aqueous workup (precipitation of the ammoniumsalts with toluene and hexane and filtration over celite).
33. Review dealing with TPAP oxidations: S. V. Ley, J. Norman, W. P. Griffith, S. P. Marsden, Synthesis 1994, 639.
34. 3) δ 15.4 (q), 16.0 (q), 17.0 (q), 19.9 (q), 20.7 (q), 26.5 (t), 28.2 (d), 32.5 (d), 32.8 (t), 35.5 (t), 38.2 (t), 41.7 (d), 44.5 (d), 44.6 (s), 47.8 (s), 53.1 (t), 65.0 (d), 80.4 (d), 173.2 (s), 176.1 (s).
35. 3).