Stereocontrolled synthesis of a sphingomyelin methylene analogue as a sphingomyelinase inhibitor

Organic Letters

Volumn 2, Issue 17, 2000, Pages 2627-2629

  Hakogi, Toshikazu ^a   Monden, Yoshiko ^a   Iwama, Seiji ^a   Katsumura, Shigeo ^a  

^a KWANSEI GAKUIN UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; ENZYME INHIBITOR; SPHINGOMYELIN; SPHINGOMYELIN PHOSPHODIESTERASE;

ARTICLE; BACILLUS CEREUS; CHEMISTRY; DRUG ANTAGONISM; STEREOISOMERISM; SYNTHESIS;

BACILLUS CEREUS; ENZYME INHIBITORS; INDICATORS AND REAGENTS; SPHINGOMYELIN PHOSPHODIESTERASE; SPHINGOMYELINS; STEREOISOMERISM;

EID: 0034710487     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006147c     Document Type: Article

References (23)

1. (a) Kolter, T.; Sandhoff, K. Angew. Chem., Int. Ed. Engl. 1999, 38, 1532.
2. (b) Sawai, H.; Hannun, Y. A. Chem. Phys. Lipids 1999, 102, 141.
3. (c) Kronke, M. Chem. Phys. Lipids 1999, 102, 157 and references cited therein.
4. Hannun, Y. A.; Bell, R. M. J. Biol. Chem. 1986, 261, 12604.
5. Murakami, M.; Iwama, S.; Fujii, S.; Ikeda, K.; Katsumura, S. Bioorg. Med. Chem. Lett. 1997, 7, 1725.
6. (a) Nara, F.; Tanaka, M.; Hosoya, T.; Suzuki-Konagai, K.; Ogita, T. J. Antibiot. 1999, 52, 525.
7. (b) Nara, F.; Tanaka, M.; Masuda-Inoue, S.; Yamasato, Y.; Doi-Yoshioka, H.; Suzuki-Konagai, K.; Kumakura, S.; Ogita, T. J. Antibiot. 1999, 52, 531.
8. (c) Uchida, R.; Tomoda, H.; Dong, Y.; Omura, S. J. Antibiot. 1999, 52, 572.
9. (d) Tanaka, M.; Nara, F.; Suzuki-Konagai, K.; Hosoya, T.; Ogita, T. J. Am. Chem. Soc. 1997, 119, 7871.
10. (a) Martin, S. F.; Josey, J. A.; Wong, Y. L.; Dean, D. W. J. Org. Chem. 1994, 59, 4805.
11. (b) Martin, S. F.; Wong, Y. L.; Wagman, A. S. J. Org. Chem. 1994, 59, 4821.
12. (a) Noyori, R.; Ikeda, T.; Ohkuma, T.; Widhalm, M.; Kitamura, M.; Takaya, H.; Akutagawa, S.; Sayo, N.; Saito, T.; Taketomi, T.; Kumobayashi, H. J. Am. Chem. Soc. 1989, 111, 9134.
13. (b) Kitamura, M.; Tokunaga, M.; Ohkuma, T.; Noyori, R. Org. Synth. 1993, 71, 1.
14. Nishizawa, M.; Garcia, D. M.; Minagawa, R.; Noguchi, Y.; Imagawa, H.; Yamada, H.; Watanabe, R.; Yoo, Y. C.; Azuma, I. Synlett 1996, 452.
15. Hatakeyama, S.; Mori, H.; Kitano, K.; Yamada, H.; Nishizawa, M. Tetrahedron Lett. 1994, 35, 4367.
16. Recently the Curtius rearrangement for the similar oxazolidinone formation was reported. (a) Pais, G. C. G.; Maier, M. E. J. Org. Chem. 1999, 64, 4551.
17. (b) Ghosh, A. K.; Hussain, K. A.; Fidanze, S. J. Org. Chem. 1997, 62, 6080.
18. (c) Ghosh, A. K.; Liu, W. J. Org. Chem. 1996, 61, 6175.
19. Ishizuka, T.; Kunieda, T. Tetrahedron Lett. 1987, 28, 4185.
20. Thomas, B. N.; Corcoran, R. C.; Cotant, C. L.; Lindemann, C. M.; Kirsch, J. E.; Persichini, P. J. J. Am. Chem. Soc. 1998, 120, 12178.
21. The major byproduct of this reaction was the vinyl ester resulting from the elimination of trimethylamine.
22. -1
23. -9 M SMase, 1 mM 2-hexadecanoylamino-4-nitrophenylphosphocholine as a substrate, and ionic strength 0.2. The detailed results will be reported elsewhere.