Polypropionates from 7-oxanorbornene derivatives. A stereoselective and divergent synthesis of fragments with four contiguous chiral centers

Tetrahedron Letters

Volumn 37, Issue 49, 1996, Pages 8957-8960

  Aceña, José Luis ^a   Arjona, Odón ^a   León, Marisa ^a   Plumet, Joaquín ^a  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

POLYMER; PROPIONIC ACID DERIVATIVE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030566783     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02057-6     Document Type: Article

References (38)

1. 1. a) Norcross, R. D.; Paterson, I. Chem. Rev. 1995, 95, 2041-2114.
2. b) Dutton, C. J.; Banks, B. J.; Cooper, C. B. Nat. Prod. Rep. 1995, 12, 165-181.
3. c) O'Hagan, D. Nat. Prod. Rep. 1995, 12, 1-32.
4. 2. For recent syntheses, see: a) Paterson, I.; Perkins, M. V. Tetrahedron 1996, 52, 1811-1834.
5. b) Nicolaou, K. C.; Patron, A. P.; Ajito, K.; Richter, P. K.; Khatuya, H.; Beitinato, P.; Miller, R, A.; Tomaszewski, M. J. Chem. Eur. J. 1996, 2, 847-868.
6. c) Kigoshi, H.; Suenaga, K.; Mutou, T.; Ishigaki, T.; Atsumi, T.; Ishiwata, H.; Sakamura, A.; Ogawa, T.; Ojika, M.; Yamada, K. J. Org. Chem. 1996, 61, 5326-5351.
7. d) Toshima, K.; Yamaguchi, H.; Jyojima, T.; Noguchi, Y.; Nakata, M.; Matsumura, S. Tetrahedron Lett. 1996, 37, 1073-1076.
8. 3. a) Lautens, M.; Belter, R. K. Tetrahedron Lett. 1992, 33, 2617-2620.
9. b) Lautens, M.; Chiu, P.; Colucci, J. T. Angew. Chem. Int. Ed. Engl. 1993, 32, 281-283.
10. c) Sevin, A.-F; Vogel, P. J. Org. Chem. 1994, 59, 5920-5926.
11. d) Yadav, J. S.; Rao, C. S.; Chandrasekhar, S.; Rama Rao, A. V. Tetrahedron Lett. 1995, 36, 7717-7720.
12. e) Kernen, P.; Vogel, P. Helv. Chim. Acta 1995, 78, 301-324.
13. f) Bialecki, M.; Vogel, P. Helv. Chim. Acta 1995, 78, 325-343.
14. g) Ancerewicz, J.; Vogel, P. Helv. Chim. Acta 1996, 79, 1393-1414.
15. 4. The terms "stereotriad", "stereotetrad", etc.; were proposed by R. W. Hoffmann as elemental subunits found in polypropionate-derived natural products: a) Hoffmann, R. W. Angew. Chem. Int. Ed. Engl. 1987, 26, 489-503.
16. For systematic approaches to the different isomers of these fragments, see: b) Paterson, I.; Channon, J. A. Tetrahedron Lett. 1992, 33, 797-800.
17. c) Domínguez, E.; Carretero, J. C. Tetrahedron 1994, 50, 7557-7566.
18. d) Marshall, J. A.; Perkins, J. F.; Wolf, M. A. J. Org. Chem. 1995, 60, 5556-5559.
19. e) Domon, L.; Vogeleisen, F.; Uguen, D. Tetrahedron Lett. 1996, 37, 2773-2776.
20. 5. a) Aceña, J. L.; Arjona, O.; Fernández de la Pradilla, R.; Plumet, J.; Viso, A. J. Org. Chem. 1992, 57, 1945-1946.
21. b) Arjona, O.; de Dios, A.; Fernández de la Pradilla, R.; Plumet, J.; Viso, A. J. Org. Chem. 1994, 59, 3906-3916.
22. 6. a) Inomata, K.; Hirata, T.; Suhara, H.; Kinoshita, H. Kotake, H.; Senda, H. Chem. Lett. 1988, 2009-2112.
23. b) Lee, S. W.; Fuchs, P. L. Tetrahedron Lett. 1991, 32, 2861-2864.
24. c) Trost, B. M.; Ghadiri, M. R. Bull. Soc. Chim. Fr. 1993, 433-442.
25. d) Fox, J. M.; Morris, C. M.; Smyth, G. D.; Whitham, G. M. J. Chem, Soc.; Perkin Trans. 1 1994, 731-737.
26. e) Marot, C.; Rollin, P. Tetrahedron Lett. 1994, 35, 8377-8380.
27. f) Short, K. M.; Ziegler Jr, C. B. Tetrahedron Lett. 1995, 36, 355-356.
28. g) Jin, Z.; Kim, S. H.; Fuchs, P. L. Tetrahedron Lett. 1996, 37, 5247-5248.
29. 7. Ogawa, S.; Iwasawa, Y.; Nose, T.; Suami, T.; Ohba, S.; Ito, M.; Saito. Y. J. Chem, Soc.; Perkin Trans. 1 1985, 903-906.
30. 8. Arjona, O.; Fernández de la Pradilla, R.; Pita-Romero, I.; Plumet, J.; Viso, A. Tetrahedron 1990, 46, 8199-8206.
31. 9. All new compounds showed spectroscopic and analytical data consistent with the assigned structures.
32. 10. Epoxidation of 7 with m-CPBA yielded a 69:31 mixture of diastereomeric oxiranes. The major product was also converted into allylic alcohol 9 by reaction with Na-Hg.
33. 11. a) Julia, M.; Paris, J.-M. Tetrahedron Lett. 1973, 4833-4836.
34. b) Kocienski, P. J. Chem. Ind. 1981, 548-551.
35. 12. Mitsunobu, O. Synthesis 1981, 1-21.
36. 13. The coupling constant between H-3 and H-4 in benzoate 13 could not be measured, although the width of their signals did not contain a constant value higher than 4-5 Hz, thus indicating the seudoaxial orientation of the benzoyl group.
37. 14. a) Schreiber, S. L.; Claus, R. E.; Reagan, J. Tetrahedron Lett. 1982, 23, 3867-3870.
38. b) Hayes, R.; Wallace, T. W. Tetrahedron Lett. 1990, 37, 3355-3356.