Synthesis of Mauritiamine

Journal of Organic Chemistry

Volumn 62, Issue 23, 1997, Pages 7918-7919

  Olofson, Anne ^a   Yakushijin, Kenichi ^a   Horne, David A ^a  

^a Och Spine at New York Presbyterian Hospitals   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000738805     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9715682     Document Type: Article

References (31)

1. For reviews, see: (a) Kobayashi, J.; Ishibashi, M. In The Alkaloids: Chemistry and Pharmacology; Brossi, A., Ed.; Academic Press: New York, 1992; Vol. 41, pp 41-124. (b) Faulkner, D. J. Nat. Prod. Rep. 1996, 13, 75. (c) Berlinck, R. G. S. Nat. Prod. Rep. 1996, 13, 377.
2. For reviews, see: (a) Kobayashi, J.; Ishibashi, M. In The Alkaloids: Chemistry and Pharmacology; Brossi, A., Ed.; Academic Press: New York, 1992; Vol. 41, pp 41-124. (b) Faulkner, D. J. Nat. Prod. Rep. 1996, 13, 75. (c) Berlinck, R. G. S. Nat. Prod. Rep. 1996, 13, 377.
3. For reviews, see: (a) Kobayashi, J.; Ishibashi, M. In The Alkaloids: Chemistry and Pharmacology; Brossi, A., Ed.; Academic Press: New York, 1992; Vol. 41, pp 41-124. (b) Faulkner, D. J. Nat. Prod. Rep. 1996, 13, 75. (c) Berlinck, R. G. S. Nat. Prod. Rep. 1996, 13, 377.
4. Tsukamoto, S.; Kato, H.; Hirota, H.; Fusetani, N. J. Nat. Prod. 1996, 59, 501.
5. (a) Forenza, S.; Minale, L.; Riccio, R.; Fattorusso, E. J. Chem. Soc., Chem. Commun. 1971, 1129.
6. (b) Garcia, E. E.; Benjamin, L. E.; Fryer, R. I. J. Chem. Soc., Chem. Commun. 1973, 78.
7. Cafieri, F.; Fattorusso, E.; Mangoni, A.; Taglialatela-Scafati, O. Tetrahedron Lett. 1996, 37, 3587.
8. Xu, Y.-z.; Yakushijin, K.; Horne, D. A. J. Org. Chem. 1997, 62, 456.
9. (a) Lancini, G. C.; Lazzari, E. J. Heterocycl. Chem. 1966, 3, 152.
10. (b) Lancini, G. C.; Lazzari, E.; Arioli, V.; Bellani, P. J. Med. Chem. 1969, 12, 775.
11. (a) Baciocchi, E.; Clementi, S.; Sebastiani, G. V. J. Chem. Soc., Perkin Trans. 2 1976, 266.
12. (b) Angelini, G.; Giancaspro, C.; Illuminati, G.; Sleiter, G. J. Org. Chem. 1980, 45, 1786.
13. In previous unpublished investigations from the Büchi group on the synthesis of saxitoxin, 4,5-dimethoxyimidazolines were obtained from the reaction of 4-acyl-2-aminoimidazoles with NBS in methanol. Dupriest, M. Ph.D. Thesis, Massachusetts Institute of Technology, 1982.
14. In the presence of base, 5 (free base) produced compound I as the major product. Chemical equation presents
15. A limited number of related dihydroxy adducts has been reported from the reaction of guanidines with glyoxal and α-dike-tones: (a) Nishimura, T.; Nakano, K.; Shibamoto, S.; Kitajima, K. J. Heterocycl. Chem. 1975, 12, 471. (b) Nishimura, T.; Kitajima, K. J. Org. Chem. 1976, 41, 1590. Nishimura, T.; Kitajima, K. J. Org. Chem. 1979, 44, 818. McClelland, R. A.; Panicucci, R.; Rauth, A. M. J. Am. Chem. Soc. 1987, 109, 4308.
16. A limited number of related dihydroxy adducts has been reported from the reaction of guanidines with glyoxal and α-dike-tones: (a) Nishimura, T.; Nakano, K.; Shibamoto, S.; Kitajima, K. J. Heterocycl. Chem. 1975, 12, 471. (b) Nishimura, T.; Kitajima, K. J. Org. Chem. 1976, 41, 1590. Nishimura, T.; Kitajima, K. J. Org. Chem. 1979, 44, 818. McClelland, R. A.; Panicucci, R.; Rauth, A. M. J. Am. Chem. Soc. 1987, 109, 4308.
17. A limited number of related dihydroxy adducts has been reported from the reaction of guanidines with glyoxal and α-dike-tones: (a) Nishimura, T.; Nakano, K.; Shibamoto, S.; Kitajima, K. J. Heterocycl. Chem. 1975, 12, 471. (b) Nishimura, T.; Kitajima, K. J. Org. Chem. 1976, 41, 1590. Nishimura, T.; Kitajima, K. J. Org. Chem. 1979, 44, 818. McClelland, R. A.; Panicucci, R.; Rauth, A. M. J. Am. Chem. Soc. 1987, 109, 4308.
18. A limited number of related dihydroxy adducts has been reported from the reaction of guanidines with glyoxal and α-dike-tones: (a) Nishimura, T.; Nakano, K.; Shibamoto, S.; Kitajima, K. J. Heterocycl. Chem. 1975, 12, 471. (b) Nishimura, T.; Kitajima, K. J. Org. Chem. 1976, 41, 1590. Nishimura, T.; Kitajima, K. J. Org. Chem. 1979, 44, 818. McClelland, R. A.; Panicucci, R.; Rauth, A. M. J. Am. Chem. Soc. 1987, 109, 4308.
19. Foley, L. H.; Büchi, G. J. Am. Chem. Soc. 1982, 104, 1776.
20. Xu, Y.-z.; Yakushijin, K.; Horne, D. A. Tetrahedron Lett. 1993, 34, 6981.
21. Irradiation of the C5 ring proton singlet at 4.73 ppm showed NOE's to both methoxyl groups (3.35 and 3.15 ppm), whereas no enhancement was observed to the methylene protons of the aminopropyl side chain.
22. Initially, the rearrangement was attempted in refluxing MeOH. The major product obtained under these conditions is compound II. Chemicals equation presented
23. All previously reported syntheses of vinyl AI derivatives related to 2 and 7 utilized Wittig chemistry in creating the olefinic double bond and relied heavily on the use of numerous protecting groups. See: (a) de Nanteuil, G.; Ahond, A.; Poupat, C.; Thoison, O.; Potier, P. Bull. Soc. Chim. Fr. 1986, 813. (b) Daninos, S.; AlMourabit, A.; Ahond, A.; Zurita, M. B.; Poupat, C.; Potier, P. Bull Soc. Chim. Fr. 1994, 131, 590. Webber, S. E.; Little, T. L. J. Org. Chem. 1994, 59, 7299.
24. All previously reported syntheses of vinyl AI derivatives related to 2 and 7 utilized Wittig chemistry in creating the olefinic double bond and relied heavily on the use of numerous protecting groups. See: (a) de Nanteuil, G.; Ahond, A.; Poupat, C.; Thoison, O.; Potier, P. Bull. Soc. Chim. Fr. 1986, 813. (b) Daninos, S.; AlMourabit, A.; Ahond, A.; Zurita, M. B.; Poupat, C.; Potier, P. Bull Soc. Chim. Fr. 1994, 131, 590. Webber, S. E.; Little, T. L. J. Org. Chem. 1994, 59, 7299.
25. All previously reported syntheses of vinyl AI derivatives related to 2 and 7 utilized Wittig chemistry in creating the olefinic double bond and relied heavily on the use of numerous protecting groups. See: (a) de Nanteuil, G.; Ahond, A.; Poupat, C.; Thoison, O.; Potier, P. Bull. Soc. Chim. Fr. 1986, 813. (b) Daninos, S.; AlMourabit, A.; Ahond, A.; Zurita, M. B.; Poupat, C.; Potier, P. Bull Soc. Chim. Fr. 1994, 131, 590. Webber, S. E.; Little, T. L. J. Org. Chem. 1994, 59, 7299.
26. Wright, A. E.; Chiles, S. A.; Cross, S. S. J. Nat. Prod. 1991, 54, 1684.
27. Compound 9 was isolated as a 9:1 mixture of erythro:threo diastereomers. The threo isomer, (2S,3S)-2-chloro-3-hydroxy-3-(2-aminoimidazol-4-yl)propylamine, is known as girolline, a potent antitumor agent isolated from the marine sponge Pseudaxinissa cantharella. (a) Ahond, A.; Bedoya-Zurita, M.; Colin, M.; Fizames, C.; Laboute, P.; Lavelle, F.; Laurent, D.; Poupat, C.; Pusset, J.; Pusset, M.; Thoison, O.; Potier, P. C. R. Seances Acad. Sci. Paris, Ser. 2 1988, 307, 145. (b) Bedoya-Surita, M.; Ahond, A.; Poupat, C.; Potier, P. Tetrahedron 1989, 45, 6713. Chiaroni, A.; Riche, C.; Ahond, A.; Poupat, C.; Pusset, M.; Potier, P. C. R. Seances Acad. Sci. Paris Ser. 2 1991, 312, 49.
28. Compound 9 was isolated as a 9:1 mixture of erythro:threo diastereomers. The threo isomer, (2S,3S)-2-chloro-3-hydroxy-3-(2-aminoimidazol-4-yl)propylamine, is known as girolline, a potent antitumor agent isolated from the marine sponge Pseudaxinissa cantharella. (a) Ahond, A.; Bedoya-Zurita, M.; Colin, M.; Fizames, C.; Laboute, P.; Lavelle, F.; Laurent, D.; Poupat, C.; Pusset, J.; Pusset, M.; Thoison, O.; Potier, P. C. R. Seances Acad. Sci. Paris, Ser. 2 1988, 307, 145. (b) Bedoya-Surita, M.; Ahond, A.; Poupat, C.; Potier, P. Tetrahedron 1989, 45, 6713. Chiaroni, A.; Riche, C.; Ahond, A.; Poupat, C.; Pusset, M.; Potier, P. C. R. Seances Acad. Sci. Paris Ser. 2 1991, 312, 49.
29. Compound 9 was isolated as a 9:1 mixture of erythro:threo diastereomers. The threo isomer, (2S,3S)-2-chloro-3-hydroxy-3-(2-aminoimidazol-4-yl)propylamine, is known as girolline, a potent antitumor agent isolated from the marine sponge Pseudaxinissa cantharella. (a) Ahond, A.; Bedoya-Zurita, M.; Colin, M.; Fizames, C.; Laboute, P.; Lavelle, F.; Laurent, D.; Poupat, C.; Pusset, J.; Pusset, M.; Thoison, O.; Potier, P. C. R. Seances Acad. Sci. Paris, Ser. 2 1988, 307, 145. (b) Bedoya-Surita, M.; Ahond, A.; Poupat, C.; Potier, P. Tetrahedron 1989, 45, 6713. Chiaroni, A.; Riche, C.; Ahond, A.; Poupat, C.; Pusset, M.; Potier, P. C. R. Seances Acad. Sci. Paris Ser. 2 1991, 312, 49.
30. Bailey, D. M.; Johnson, R. E. J. Med. Chem. 1973, 16, 1300.
31. 13C chemical shifts between neutral and protonated glycocyamidine derivatives, which will be the subject of a future publication.