Practical Synthesis of KRN7000 from Phytosphingosine

Sanghee Kim; Soyoung Song; Taeho Lee; Sungkyu Jung; Deukjoon Kim

doi:10.1055/s-2004-822315

PAPER

Practical Synthesis of KRN7000 from Phytosphingosine

Sanghee Kim*^a,b, Soyoung Song^a,b, Taeho Lee^a, Sungkyu Jung^a, Deukjoon Kim^b
^a Natural Products Research Institute, College of Pharmacy, Seoul National University, 28 Yungun, Jongro, Seoul 110-460, Korea
Fax: +82(2)7628322; e-Mail: pennkim@snu.ac.kr;
^b College of Pharmacy, Seoul National University, San 56-1, Shilim, Kwanak, Seoul 151-742, Korea

Abstract

Alle Artikel dieser Rubrik

Abstract

The efficient and practical synthesis of the biologically important α-galactosylceramides, KRN7000, from phytosphingosine has been achieved in six steps in high overall yield.

Key words

sphingolipids - glycosylations - glycolipids - natural products - antitumor agents

Volltext

Referenzen

References

1 For a good review with citations to recent work, see: Shimosaka A. Int. J. Hematol. 2002, 76: 277

2 Vo-Hong Y. Micouin L. Ronet C. Gachelin G. Bonin M. ChemBioChem 2003, 4: 27 ; and reference cited therein

3 Hayakawa Y. Rovero S. Forni G. Smyth MJ. Proc. Natl. Acad. Sci. U.S.A. 2003, 100: 9464

4 Godfrey DI. Hammond KJ. Poulton LD. Smyth MJ. Baxter AG. Immunol. Today 2000, 21: 573

5 Zhou X.-T. Forestier C. Goff RD. Li C. Teyton L. Bendelac A. Savage PB. Org. Lett. 2002, 4: 1267

6 Morita M. Motoki K. Akimoto K. Natori T. Sakai T. Sawa E. Yamaji K. Koezuka Y. Kobayashi E. Fukushima H. J. Med. Chem. 1995, 38: 2176

7 Sakai T. Ehara H. Koezuka Y. Org. Lett. 1999, 1: 359

8 Sakai T. Naidenko OV. Iijima H. Kronenberg M. Koezuka Y. J. Med. Chem. 1995, 38: 1836

9a Kawano T. Cui J. Koezuka Y. Toura I. Kaneko Y. Motoki K. Ueno H. Nakagawa R. Sato H. Kondo E. Koseki H. Taniguchi M. Science 1997, 278: 1626

9b Sharif S. Arreaza GA. Zucker P. Mi Q.-S. Sondhi J. Naidenko OV. Kronenberg M. Koezuka Y. Delovitch TL. Nature Med. 2001, 7: 1057

9c Hong S. Wilson MT. Serizawa I. Wu L. Nagendra S. Naidenko O. Miura T. Haba T. Scherer DC. Wie J. Kronenberg M. Koezuka Y. van Kaer L. Nature Med. 2001, 7: 1052

For synthesis of KRN7000, see:

10a Morita M. Natori T. Akimoto K. Osawa T. Fukushima H. Koezuka Y. Bioorg. Med. Chem. Lett. 1995, 5: 699

10b Figueroa-Pérez S. Schmidt RR. Carbohydr. Res. 2000, 328: 95

10c Takikawa H. Muto S.-E. Mori K. Tetrahedron 1998, 54: 3141

10d Plettenburg O. Bodmer-Narkevitch V. Wong C.-H. J. Org. Chem. 2002, 67: 4559 ; and ref. 6

11 Vinogradova EI. Lipkin VM. Alakhov YB. Feigina MY. Shvetsov YB. Zh. Obsh. Khim. 1968, 38: 777

12 Nicolaou KC. Caulfield T. Kataoka K. Kumazawa TA. J. Am. Chem. Soc. 1988, 110: 7910

13a Mottawia MS. Olsen CE. Denyer K. Smith AM. Moller BL. Carbohydr. Res. 2001, 330: 309

13b Wegmann B. Schmidt RR. J. Carbohydr. Chem. 1987, 6: 357