Intramolecular 1,3-Dipolar Cycloadditions of Sugar Ketonitrones: A Convenient Method for Stereoselective Formation of Nitrogenated Quaternary Centers

Journal of Organic Chemistry

Volumn 62, Issue 20, 1997, Pages 6710-6711

  Torrente, S ^a   Noya, B ^a   Paredes, M D ^a   Alonso, R ^a  

^a UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000118768     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9710893     Document Type: Article

References (24)

1. (a) For a general treatise see Cycloaddition Reactions in Organic Synthesis; Carruthers, W., Ed.; Tetrahedron Organic Chemistry Series, Vol. 8, Pergamon Press; New York, 1990.
2. (b) See also Advances in Cycloaddition; Vol. 1 (1988), Vol. 2 (1990), and Vol. 3 (1993); Curran, D. P., Ed.; Jai Press Inc.: London.
3. (c) An extensive review of the synthetic utility of cycloaddition reactions can be found in Comprehensive Organic Synthesis; Trost, B., Ed.; Pergamon Press: New York, 1992; Vol. 5. In Vol. 4 of the same collection, A. Padwa reviews intermolecular 1,3-dipolar cycloadditions (Chapter 4.9, pp 1069-1109), and P. A. Wade reviews intramolecular 1,3-dipolar cycloadditions (Chapter 4.10, pp 1111-1168). See also Confalone, P. N.; Huie, E. M. Org. React. 1988, 36, 1-173.
4. (c) An extensive review of the synthetic utility of cycloaddition reactions can be found in Comprehensive Organic Synthesis; Trost, B., Ed.; Pergamon Press: New York, 1992; Vol. 5. In Vol. 4 of the same collection, A. Padwa reviews intermolecular 1,3-dipolar cycloadditions (Chapter 4.9, pp 1069-1109), and P. A. Wade reviews intramolecular 1,3-dipolar cycloadditions (Chapter 4.10, pp 1111-1168). See also Confalone, P. N.; Huie, E. M. Org. React. 1988, 36, 1-173.
5. The mechanisms of two of the most important cycloaddition reactions (the Diels-Alder reaction and the 1,3-dipolar cycloaddition) are discussed from a historical perspective (1935-1995) in Houk, K. N.; González, J.; Li, Y. Ace. Chem. Res. 1995, 28, 81-90.
6. (a) For a monograph, see Cycloaddition Reactions in Carbohydrate Chemistry; Giuliano, R. M., Ed.; ACS Symposium Series No. 494, 1992.
7. (b) For a discussion of the applications of cycloaddition reactions in the transformation of carbohydrate derivatives into functionalized cyclohexanes and cyclopentanes, see Ferrier, R. J.; Middleton, S. Chem. Rev. 1993, 93, 2779-2831.
8. Tetrodotoxin, Saxitoxin and the Molecular Biology of the Sodium Channel; Annals of The New York Academy of Sciences; Kao, C. Y., Levinson, S. R., Eds.; New York Academy of Sciences: New York, 1986; Vol. 479. To date only one total synthesis of tetrodotoxin in racemic form has been accomplished: Kishi, Y.; Aratani, M.; Fukuyama, T.; Nakatsubo, F.; Goto, T.; Inoue, S.; Tanino, H.; Sugiure, S.; Kakoi, H. J. Am. Chem. Soc. 1972, 94, 9217. Ibid. 1972, 94, 9219.
9. Tetrodotoxin, Saxitoxin and the Molecular Biology of the Sodium Channel; Annals of The New York Academy of Sciences; Kao, C. Y., Levinson, S. R., Eds.; New York Academy of Sciences: New York, 1986; Vol. 479. To date only one total synthesis of tetrodotoxin in racemic form has been accomplished: Kishi, Y.; Aratani, M.; Fukuyama, T.; Nakatsubo, F.; Goto, T.; Inoue, S.; Tanino, H.; Sugiure, S.; Kakoi, H. J. Am. Chem. Soc. 1972, 94, 9217. Ibid. 1972, 94, 9219.
10. Tetrodotoxin, Saxitoxin and the Molecular Biology of the Sodium Channel; Annals of The New York Academy of Sciences; Kao, C. Y., Levinson, S. R., Eds.; New York Academy of Sciences: New York, 1986; Vol. 479. To date only one total synthesis of tetrodotoxin in racemic form has been accomplished: Kishi, Y.; Aratani, M.; Fukuyama, T.; Nakatsubo, F.; Goto, T.; Inoue, S.; Tanino, H.; Sugiure, S.; Kakoi, H. J. Am. Chem. Soc. 1972, 94, 9217. Ibid. 1972, 94, 9219.
11. We recently reported a free radical approach to the formation of the quaternary C8a center of this molecule: Noya, B.; Alonso, R. Tetrahedron Lett. 1997, 38, 2745. This paper lists references relating to the main attempts at development of a total synthesis of the enantiomerically pure toxin and to the recent isolation of new congeners.
12. (+)-Lactacystin was recently reported as the first non-protein neurotrophic factor: Omura, S.; Fujimoto, T.; Otoguro, K.; Matsuzaki, K.; Moriguchi, R.; Tanaka, H.; Sasaki, Y. J. Antibiot. 1991, 44, 113. For a discussion of the main attempts at total synthesis of (+)lactacystin, see Casiraghi, G.; Rassu, G.; Zanardi, F. Chemtracts-Org. Chem. 1994, 266-272. See also: Fenteany, G.; Standaert, R. F.; Lane, W. S.; Choi, S.; Corey, E. J.; Schreiber, S. L. Science 1995, 268, 726 and references cited therein.
13. (+)-Lactacystin was recently reported as the first non-protein neurotrophic factor: Omura, S.; Fujimoto, T.; Otoguro, K.; Matsuzaki, K.; Moriguchi, R.; Tanaka, H.; Sasaki, Y. J. Antibiot. 1991, 44, 113. For a discussion of the main attempts at total synthesis of (+)lactacystin, see Casiraghi, G.; Rassu, G.; Zanardi, F. Chemtracts-Org. Chem. 1994, 266-272. See also: Fenteany, G.; Standaert, R. F.; Lane, W. S.; Choi, S.; Corey, E. J.; Schreiber, S. L. Science 1995, 268, 726 and references cited therein.
14. (+)-Lactacystin was recently reported as the first non-protein neurotrophic factor: Omura, S.; Fujimoto, T.; Otoguro, K.; Matsuzaki, K.; Moriguchi, R.; Tanaka, H.; Sasaki, Y. J. Antibiot. 1991, 44, 113. For a discussion of the main attempts at total synthesis of (+)lactacystin, see Casiraghi, G.; Rassu, G.; Zanardi, F. Chemtracts-Org. Chem. 1994, 266-272. See also: Fenteany, G.; Standaert, R. F.; Lane, W. S.; Choi, S.; Corey, E. J.; Schreiber, S. L. Science 1995, 268, 726 and references cited therein.
15. For the 1,3-dipolar cycloaddition of glycosyl aldonitrones, see Fisera, L.; Al-Timari, V. A. R.; Ertl, P. in ref 2a, Chapter 11. For a recent review of asymmetric cycloadditions of nitrones, including sugar-derived aldonitrones, see Frederickson, M. Tetrahedron 1997, 53, 403.
16. For the 1,3-dipolar cycloaddition of glycosyl aldonitrones, see Fisera, L.; Al-Timari, V. A. R.; Ertl, P. in ref 2a, Chapter 11. For a recent review of asymmetric cycloadditions of nitrones, including sugar-derived aldonitrones, see Frederickson, M. Tetrahedron 1997, 53, 403.
17. Tronchet, J. M. J.; Mihaly, M. E. Helv. Chim. Acta 1972, 55, 1266. See also ref 11.
18. Cerny, M.; Stanek, J., Jr. Adv. Carbohydr. Chem. 1977, 34, 23-177.
19. 2 (16 mL) was refluxed for 28 h. The organic phase was washed with water, dried, and concentrated. Flash chromatography of the residue afforded isoxazolidine 17 (485 mg, 79%).
20. Formation of a nitrogenated quaternary center at position C5 of a glucofuranose derivative analogous to 19 (by trichloroacetimidate rearrangement), and final conversion to (+)-lactacystin, has recently been reported: Chida, N.; Takeoka, J.; Tsutsumi, N.; Ogawa, S. J. Chem. Soc., Chem. Commun. 1995, 793.
21. In the course of this work, a related 1,3-dipolar cycloaddition was reported for the furanose of nucleoside derivatives: Kong, J.; Roselt, P.; Plavec, J.; Chaltopadhyaya, J. Tetrahedron 1994, 50, 4921.
22. (a) Datta, S.; Chattopadyay, P.; Mukhopadhyay, T.; Bhattacharjya, A. Tetrahedron Lett. 1993, 34, 3585.
23. (b) Shing, T. K. M.; Wong, C.; Yip, T. Tetrahedron: Asymmetry 1996, 7, 1323,
24. The high yield obtained in the cycloaddition of 19 strongly suggests that a synthetic approach to (+)-lactacystin and/or lactacystin analogues based on this methodology would be viable (see also note 10).