Stereoselective synthesis of the polar part of mycestericins E and G

Chemical Papers

Volumn 65, Issue 4, 2011, Pages 527-535

  Martinková, Miroslava ^a   Gonda, Jozef ^a   Uhríková, Alena ^a   Kovácová, Margaréta ^a  

^a P J AFÁRIK UNIVERSITY   (Slovakia)

Author keywords

amino acid; Immunosuppressant; Mycestericins; Stereoselective synthesis

Indexed keywords

EID: 80051789122     PISSN: 03666352     EISSN: 13369075     Source Type: Journal    
DOI: 10.2478/s11696-011-0030-5     Document Type: Article

References (18)

1. Byun, H.-S., Lu, X., & Bittman, R. (2006). Stereoselective total synthesis of serine palmitoyl-CoA transferase inhibitors. Synthesis, 15, 2447-2474. DOI: 10.1055/s-2006-942475. (Pubitemid 44229458)
2. Delgado, A., Casas, J., Llebaria, A., Abad, J. L., & Fabrias, G. (2006). Inhibitors of sphingolipid metabolism enzymes. Biochimica et Biophysica Acta (BBA) -Biomembranes, 1758, 1957-1977. DOI: 10.1016/j.bbamem.2006.08.017. (Pubitemid 44879369)
3. Fujita, T., Hamamichi, N., Kiuchi, M., Matsuzaki, T., Kitao, Y., Inoue, K., Hirose, R., Yoneta, M., Sasaki, S., & Chiba, K. (1996). Determination of absolute configuration and biological activity of new immunosuppressants, mycestericins D, E, F and G. The Journal of Antibiotics, 49, 846-853. (Pubitemid 26348495)
4. Fujita, T., Hamamichi, N., Matsuzaki, T., Kitao, Y., Kiuchi, M., Node, M., & Hirose, R. (1995). Determination of the absolute configurations and the total synthesis of new immunosuppressants, mycestericins E and G. Tetrahedron Letters, 36, 8599-8602. DOI: 10.1016/0040-4039(95)01823-Z.
5. Hanada, K. (2003). Serine palmitoyltransferase, a key enzyme of sphingolipid metabolism. Biochimica et Biophysica Acta (BBA) -Molecular and Cell Biology of Lipids, 1632, 16-30. DOI: 10.1016/S1388-1981(03)00059-3. (Pubitemid 36628112)
6. Iwabuchi, Y., Furukawa, M., Esumi, T., & Hatakeyama, S. (2001). An enantio-and stereocontrolled synthesis of (-)-mycestericin E via cinchona alkaloid-catalyzed asymmetric Baylis-Hillman reaction. Chemical Communications, 2001, 2030-2031. DOI: 10.1039/b106471c. (Pubitemid 32964567)
7. Jones, M. C., & Marsden, S. P. (2008). Total synthesis of the immunosuppressants myriocin and 2-epi-myriocin. Organic Letters, 10, 4125-4128. DOI: 10.1021/ol801709c.
8. Martinkova, M., Gonda, J., & Raschmanova, J. (2006). Novel furanoid a-substituted a-amino acid as a potent turn mimic in peptide synthesis. Molecules, 11, 564-573. DOI: 10.3390/11070564. (Pubitemid 44252746)
9. Martinkova, M., Gonda, J., Raschmanova, J., & Vojticková, M. (2007). The efficient preparation of a-substituted serine scaffolds as the chiral building blocks for the synthesis of SPT inhibitors. Tetrahedron, 63, 10603-10607. DOI: 10.1016/j.tet.2007.08.019. (Pubitemid 47374269)
10. Miyake, Y., Kozutsumi, Y., Nakamura, S., Fujita, T., & Kawasaki, T. (1995). Serine palmitoyltransferase is the primary target of a sphingosine-like immunosuppressants, ISP-1/myriocin. Biochemical and Biophysical Research Communications, 211, 396-403. DOI: 10.1006/bbrc.1995.1827.
11. Muto, S.-e., & Mori, K. (2001). Synthesis of posticlure [(6Z,9Z,11S,12S)-11,12-epoxyhenicosa-6,9-diene], the female sex pheromone of Orgyia postica. European Journal of Organic Chemistry, 2001, 4635-4638. DOI: 10.1002/1099-0690(200112)2001:24<4635::AID-EJOC4635>3.0.CO;2-J. (Pubitemid 33726860)
12. Nishide, K., Shibata, K., Fujita, T., Kajimoto, T., Wong, C.-H., & Node, M. (2000). An asymmetrical total synthesis of a potent immunosuppressant, mycestericins D and F, through an aldol reaction using L-threonine aldolase. Heterocycles, 52, 1191-1201. DOI: 10.3987/COM-99-S117.
13. Oishi, T., Ando, K., Inomiya, K., Sato, H., Iida, M., & Chida, N. (2002). Total synthesis of (+)-myriocin and (-)-sphingofungin E from aldohexoses using Overman rearrangement as the key reaction. Bulletin of the Chemical Society of Japan, 75, 1927-1947. DOI: 10.1246/bcsj.75.1927.
14. Sasaki, S., Hashimoto, R., Kiuchi, M., Inoue, K., Ikumoto, T., Hirose, R., Chiba, K., Hoshino, Y., Okumoto, T., & Fujita, T. (1994). Fungal metabolites. Part 14. Novel potent immunosuppressants, mycestericins, produced by Mycelia sterilia. The Journal of Antibiotics, 47, 420-433.
15. Satam, V., Harad, A., Rajule, R., & Pati, H. (2010). 2-Iodoxybenzoic acid (IBX): An efficient hypervalent iodine reagent. Tetrahedron, 66, 7659-7706. DOI: 10.1016/j.tet.2010. 07.014.
16. Sato, H., Sato, K., Iida, M., Yamanaka, H., Oishi, T., & Chida, N. (2008). Total synthesis of mycestericin A. Tetrahedron Letters, 49, 1943-1947. DOI: 10.1016/j.tetlet.2008.01.105. (Pubitemid 351258122)
17. Shibata, K., Shingu, K., Vassilev, V. P., Nishide, K., Fujita, T., Node, M., Kajimoto, T., & Wong, C.-H. (1996). Kinetic and thermodynamic control of L-threonine aldolase catalyzed reaction and its application to the synthesis of mycestericin D. Tetrahedron Letters, 37, 2791-2794. DOI: 10.1016/0040-4039(96) 00430-3. (Pubitemid 26127797)
18. Yamanaka, H., Sato, K., Sato, H., Iida, M., Oishi, T., & Chida, N. (2009). Total synthesis of mycestericin A and its 14-epimer. Tetrahedron, 65, 9188-9201. DOI: 10.1016/j.tet.2009. 09.012.