Organic Letters
Letter
(19) (a) Kobayashi, Y.; Okui, H. J. Org. Chem. 2000, 65, 612−615.
(b) Kang, T.; Song, S. B.; Kim, W.-Y.; Kim, B. G.; Lee, H.-Y. J. Am.
Chem. Soc. 2014, 136, 10274−10276.
AUTHOR INFORMATION
■
Corresponding Author
(20) Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 48, 4155−4156.
(21) Gil, L.; Han, Y. X.; Opas, E. E.; Rodan, G. A.; Ruel, R.; Seedor, J.
G.; Tyler, P. C.; Young, R. N. Bioorg. Med. Chem. 1999, 7, 901−919.
(22) Uragami, M.; Tokutake, N.; Yan, X.; Regen, S. L. J. Am. Chem.
Soc. 2001, 123, 5124−5125.
Notes
The authors declare no competing financial interest.
(23) Masuda, Y.; Mori, K. Eur. J. Org. Chem. 2005, 2005, 4789−4800.
(24) Pandey, A. K.; Naduthambi, D.; Thomas, K. M.; Zondlo, N. J. J.
Am. Chem. Soc. 2013, 135, 4333−4363.
ACKNOWLEDGMENTS
■
This work was supported by the Czech Science Foundation
(13-23891S) and Charles University in Prague (GAUK
1868214 and SVV 2015-260-183). We are grateful to Assoc.
(25) Sunitha, S.; Kanjilal, S.; Reddy, P. S.; Prasad, R. B. N.
Tetrahedron Lett. 2007, 48, 6962−6965.
(26) Dhimitruka, H.; SantaLucia, J. Org. Lett. 2006, 8, 47−50.
(27) Masuda, Y.; Mori, K. J. Indian Chem. Soc. 2003, 80, 1081−1083.
(28) (a) Behne, M.; Uchida, Y.; Seki, T.; de Montellano, P. O.; Elias,
P. M.; Holleran, W. M. J. Invest. Dermatol. 2000, 114, 185−192.
(b) Bleck, O.; Abeck, D.; Ring, J.; Hoppe, U.; Vietzke, J.-P.; Wolber,
R.; Brandt, O.; Schreiner, V. J. Invest. Dermatol. 1999, 113, 894−900.
(c) Hamanaka, S.; Hara, M.; Nishio, H.; Otsuka, F.; Suzuki, A.;
Uchida, Y. J. Invest. Dermatol. 2002, 119, 416−423. (d) Uchida, Y.;
Hara, M.; Nishio, H.; Sidransky, E.; Inoue, S.; Otsuka, F.; Suzuki, A.;
Elias, P. M.; Holleran, W. M.; Hamanaka, S. J. Lipid Res. 2000, 41,
2071−2082.
(29) (a) Masukawa, Y.; Narita, H.; Sato, H.; Naoe, A.; Kondo, N.;
Sugai, Y.; Oba, T.; Homma, R.; Ishikawa, J.; Takagi, Y.; Kitahara, T. J.
Lipid Res. 2009, 50, 1708−1719. (b) Ishikawa, J.; Narita, H.; Kondo,
N.; Hotta, M.; Takagi, Y.; Masukawa, Y.; Kitahara, T.; Takema, Y.;
Koyano, S.; Yamazaki, S.; Hatamochi, A. J. Invest. Dermatol. 2010, 130,
2511−2514. (c) Janssens, M.; van Smeden, J.; Gooris, G. S.; Bras, W.;
Portale, G.; Caspers, P. J.; Vreeken, R. J.; Kezic, S.; Lavrijsen, A. P. M.;
Bouwstra, J. A. J. Invest. Dermatol. 2011, 131, 2136−2138. (d) t’Kindt,
R.; Jorge, L.; Dumont, E.; Couturon, P.; David, F.; Sandra, P.; Sandra,
K. Anal. Chem. 2012, 84, 403−411.
Prof. L. Novak
for measuring IR spectra, and V. Hronova
University in Prague, Faculty of Pharmacy in Hradec Kral
́
ova
́
for measuring HRMS spectra, I. Vencovska
(all from the Charles
ove,
́
́
́
́
Czech Republic) for conducting elemental analysis.
REFERENCES
■
(1) (a) Hannun, Y. A. Science 1996, 274, 1855−1859. (b) Hannun, Y.
A.; Obeid, L. M. Nat. Rev. Mol. Cell Biol. 2008, 9, 139−150.
(2) Candi, E.; Schmidt, R.; Melino, G. Nat. Rev. Mol. Cell Biol. 2005,
6, 328−340.
(3) Rabionet, M.; Gorgas, K.; Sandhoff, R. Biochim. Biophys. Acta,
Mol. Cell Biol. Lipids 2014, 1841, 422−434.
(4) (a) Poulos, A. Lipids 1995, 30, 1−14. (b) Sandhoff, R. FEBS Lett.
2010, 584, 1907−1913.
(5) Jakobsson, A.; Westerberg, R.; Jacobsson, A. Prog. Lipid Res.
2006, 45, 237−249.
(6) Jennemann, R.; Rabionet, M.; Gorgas, K.; Epstein, S.; Dalpke, A.;
Rothermel, U.; Bayerle, A.; van der Hoeven, F.; Imgrund, S.; Kirsch, J.
Hum. Mol. Genet. 2012, 21, 586.
(7) Elias, P. M.; Goerke, J.; Friend, D. S. J. Invest. Dermatol. 1977, 69,
535−546.
(8) (a) Uchida, Y.; Holleran, W. M. J. Dermatol. Sci. 2008, 51, 77−87.
(b) Feingold, K. R.; Elias, P. M. Biochim. Biophys. Acta, Mol. Cell Biol.
Lipids 2014, 1841, 280−294.
(9) Vasireddy, V.; Uchida, Y.; Salem, N.; Kim, S. Y.; Mandal, M. N.
A.; Reddy, G. B.; Bodepudi, R.; Alderson, N. L.; Brown, J. C.; Hama,
H. Hum. Mol. Genet. 2007, 16, 471−482.
(10) (a) Holleran, W. M.; Takagi, Y.; Uchida, Y. FEBS Lett. 2006,
580, 5456−5466. (b) Breiden, B.; Sandhoff, K. Biochim. Biophys. Acta,
Mol. Cell Biol. Lipids 2014, 1841, 441−452.
(11) van Smeden, J.; Hoppel, L.; van der Heijden, R.; Hankemeier,
T.; Vreeken, R. J.; Bouwstra, J. A. J. Lipid Res. 2011, 52, 1211−1221.
(12) Hansen, H. S.; Jensen, B. Biochim. Biophys. Acta, Lipids Lipid
Metab. 1985, 834, 357−363.
(13) (a) Mori, K.; Matsuda, H. Liebigs Ann. Chem. 1991, 1991, 529−
535. (b) Muller, S.; Schmidt, R. R. J. Prakt. Chem. 2000, 342, 779−784.
(c) Tashiro, T.; Mori, K. Biosci., Biotechnol., Biochem. 2012, 76, 1715−
1720.
(14) Kovacik, A.; Roh, J.; Vavrova, K. ChemBioChem 2014, 15,
1555−1562.
(15) (a) Chun, J.; Byun, H.-S.; Bittman, R. J. Org. Chem. 2003, 68,
348−354. (b) Yadav, J. S.; Geetha, V.; Raju, A. K.; Gnaneshwar, D.;
Chandrasekhar, S. Tetrahedron Lett. 2003, 44, 2983−2985. (c) Mori,
K.; Masuda, Y. Tetrahedron Lett. 2003, 44, 9197−9200.
(16) (a) Masukawa, Y.; Narita, H.; Shimizu, E.; Kondo, N.; Sugai, Y.;
Oba, T.; Homma, R.; Ishikawa, J.; Takagi, Y.; Kitahara, T.; Takema, Y.;
Kita, K. J. Lipid Res. 2008, 49, 1466−1476. (b) Doering, T.; Holleran,
W. M.; Potratz, A.; Vielhaber, G.; Elias, P. M.; Suzuki, K.; Sandhoff, K.
J. Biol. Chem. 1999, 274, 11038−11045.
(17) Mori, K.; Nishio, H. Liebigs Ann. Chem. 1991, 1991, 253−257.
(18) (a) Mun, J.; Onorato, A.; Nichols, F. C.; Morton, M. D.; Saleh,
A. I.; Welzel, M.; Smith, M. B. Org. Biomol. Chem. 2007, 5, 3826−
3833. (b) Novotny, J.; Pospechova, K.; Hrabalek, A.; Cap, R.; Vavrova,
K. Bioorg. Med. Chem. Lett. 2009, 19, 6975−6977.
D
Org. Lett. XXXX, XXX, XXX−XXX