An efficient synthesis of the natural tetrahyclrofuran pachastrissamine starting from D-ribo-phytosphingosine

Journal of Organic Chemistry

Volumn 71, Issue 2, 2006, Pages 836-839

  Van Tien Berg, Richard J B H N ^a   Boltje, Thomas J ^a   Verhagen, Carlo P ^a   Litjens, Remy E J N ^a   Van Der Marel, Gijsbert A ^a   Overkleeft, Herman S ^a  

^a LEIDEN UNIVERSITY   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; CARCINOGENS; CELLS; CYTOLOGY; DERIVATIVES; SYNTHESIS (CHEMICAL); TOXIC MATERIALS;

ANHYDROPHYTOSPHINGOSINE; NATURAL PRODUCT; PACHASTRISSAMINE; SPONGES;

NATURAL POLYMERS;

PACHASTRISSAMINE; PHYTOSPHINGOSINE; TETRAHYDROFURAN; UNCLASSIFIED DRUG;

ARTICLE; CARCINOMA CELL; CYTOTOXICITY; DRUG SYNTHESIS; QUANTUM YIELD; SPONGE (PORIFERA);

FURANS; INDICATORS AND REAGENTS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; RIBOSE; SPHINGOSINE;

EID: 30744465348     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0520240     Document Type: Article

References (21)

1. (a) Lynch, D. V.; Dunn, T. M. New Phytol. 2004, 161, 677-702.
2. (b) Dickson, R. C.; Lester, R. L. Biochim. Biophys. Acta 1999, 1438, 305-321.
3. (c) Dickson, R. C.; Lester, R. L. Biochim. Biophys. Acta 1999, 1426, 347-357.
4. (d) Sweely, C. C. In Biochemistry of Lipid, Lipoproteins, and Membranes, Vance, D. E., Vance, J, E., Eds.; Elsevier: Amsterdam, 1991.
5. (a) Jenkins, G. M. Cell. Mol. Life Sci. 2003, 60, 701-710.
6. (b) Jenkins, G. M.; Hannun, Y. A. J. Biol. Chem. 2001, 276, 8574-8581.
7. (c) Chung, N.; Jenkins, G. M.; Hannun, Y. A.; Heitman, J.; Obeid, L. M. J. Biol. Chem. 2000, 275, 17229-17232.
8. Liao, J.; TaO, J.; Lin, G.; Lin, D. Tetrahedron 2005, 61, 4715-4733.
9. Shibano, M.; Tsukamoto, D.; Kusano, G. Heterocycles 2002, 57, 1539-1553 and references therein.
10. (a) Kuroda, I.; Musman, M.; Ohlani, I. I.; lehiba, T.; Tanaka, J.; Gravalos, D. G.; Higa, T. J. Nat. Prod. 2002, 05, 1505-1506.
11. (b) Ledroit, V.; Debitus, C.; Lavmid, C.; Massiot, G, Tetrahedron Lett. 2003, 44, 225-228.
12. Phytosphingosine [(2S.3S,4R)-2-amino-1,3,4-octadecauetriol] was a gift from Degussa Cosmolerm B.V., The Netherlands. For more information see the Supporting Information.
13. (a) van den Berg, R. J. B. H. N.; Korevaar, C. G. N.; Overkleeft, H, S.; van der Marel, G. A.; van Boom, J. H. J. Org. Chem. 2004, 69, 5699-5704.
14. (b) van den Berg, R. J. B. H. N.; Korevaar, C. G. N.; van der Marel, G. A.; Overkleeft, H. S.; van Boom, J. H. Tetrahedron Lett. 2002, 43, 8409-8412.
15. This anhydrophytosphingosine analogue has been reported as a derivative of a plant metabolite: O'Connell, P, W.; Tsien, S. H. Arch. Biochem. Biophys. 1959, 80, 289-294.
16. (a) Alper, P. B.; Hung, S. C.; Wong, C.-H. Tetrahedron Lett. 1996, 37, 6029-6032.
17. (b) Vasella, A.; Witzig, C.; Chiara, J.-L.; Martin-Lomas, M.; Helv. Chim. Acta 1991, 74, 2073-2077.
18. Zheng, T.; Naraynn, R. S.; Schomaker, J. M.; Borhan, B. J. Am. Chem. Soc. 2005, 127, 6946-6947.
19. The spectral and analytical data of compounds 3 and 14 are in complete accordance with the reported data; see refs 5b and 12a.
20. (a) Sudhakar, N.; Ravi Kumar, A.; Prabhakar, A.; Jagadeesh, B.; Venkateswara Rao, B. Tetrahedron Lett. 2005, 46, 328-327.
21. (b) Bhaket, P.; Morris, K.; Stauffer, C. S.; Datta, A. Org. Lett. 2005, 7, 875-876.