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Volumn 30, Issue 1, 2007, Pages 22-27

A concise synthesis of a promising protein kinase C inhibitor: D-erythro-sphingosine

Author keywords

Amino alcohol; Ceramide; Sphingolipid; Sphingosine

Indexed keywords

AMIDE; DRUG DERIVATIVE; ERYTHRO (2R,3S) SPHINGOSINE; ERYTHRO-(2R,3S)-SPHINGOSINE; KETONE; PROTEIN KINASE C; PROTEIN KINASE INHIBITOR; SERINE; SPHINGOSINE;

EID: 33846813433     PISSN: 02536269     EISSN: None     Source Type: Journal    
DOI: 10.1007/BF02977774     Document Type: Article
Times cited : (12)

References (27)
  • 1
    • 0037074113 scopus 로고    scopus 로고
    • A concise route to D-erythro-sphingosine from N-Boc-L-serine derivatives via sulfoxide or sulfone intermediates
    • Bittman, R., Chun, J., Li, G., and Byun, H. S., A concise route to D-erythro-sphingosine from N-Boc-L-serine derivatives via sulfoxide or sulfone intermediates. Tetrahedron Letters, 43, 375-377 (2002).
    • (2002) Tetrahedron Letters , vol.43 , pp. 375-377
    • Bittman, R.1    Chun, J.2    Li, G.3    Byun, H.S.4
  • 2
    • 13944283368 scopus 로고    scopus 로고
    • Efficient and versatile synthesis of (2S,3R)-sphingosine and its 2-azido-3-O-benzylsphingosine analogue
    • Bittman, R. and Lu, X., Efficient and versatile synthesis of (2S,3R)-sphingosine and its 2-azido-3-O-benzylsphingosine analogue. Tetrahedron Letters, 46, 1873-1875 (2005).
    • (2005) Tetrahedron Letters , vol.46 , pp. 1873-1875
    • Bittman, R.1    Lu, X.2
  • 3
    • 0034602328 scopus 로고    scopus 로고
    • Stereoselective preparation of ceramide and its skeleton backbone modified analogues via cyclic thionocarbonate intermediates derived by catalytic asymmetric dihydroxylation of α,β-unsaturated ester precursors
    • Bittman, R., He, L., and Byun, H. S., Stereoselective preparation of ceramide and its skeleton backbone modified analogues via cyclic thionocarbonate intermediates derived by catalytic asymmetric dihydroxylation of α,β-unsaturated ester precursors. J. Org. Chem., 65, 7627-7633 (2000).
    • (2000) J. Org. Chem , vol.65 , pp. 7627-7633
    • Bittman, R.1    He, L.2    Byun, H.S.3
  • 4
    • 0037064401 scopus 로고    scopus 로고
    • A simple and low cost synthesis of D-erythro- sphingosine and D-erythro-azidosphingosine from D-ribo- phytosphingosine:glycosphingolipid precursors
    • Boom, J. H., Berg, R. J., Korevaar, C. G. N., Marel, G. A., and Overkleeft, H. S., A simple and low cost synthesis of D-erythro- sphingosine and D-erythro-azidosphingosine from D-ribo- phytosphingosine:glycosphingolipid precursors. Tetrahedron Letters, 43, 8409-8412 (2002).
    • (2002) Tetrahedron Letters , vol.43 , pp. 8409-8412
    • Boom, J.H.1    Berg, R.J.2    Korevaar, C.G.N.3    Marel, G.A.4    Overkleeft, H.S.5
  • 5
    • 0037155732 scopus 로고    scopus 로고
    • A short and efficient stereoselective synthesis of all four diastereomers of sphingosine
    • Chung, S. K., Lee, J. M., and Lim, H. S., A short and efficient stereoselective synthesis of all four diastereomers of sphingosine. Tetrahedron: Asymmetry, 13, 343-347 (2002).
    • (2002) Tetrahedron: Asymmetry , vol.13 , pp. 343-347
    • Chung, S.K.1    Lee, J.M.2    Lim, H.S.3
  • 6
    • 30144438606 scopus 로고    scopus 로고
    • An efficient synthesis of D-erythro- and D-threo-sphingosine from D-glucose: Olefin cross-metathesis approach
    • Dhavale, D. D., Chaudhari, V. D., and Kumar, K. S. A., An efficient synthesis of D-erythro- and D-threo-sphingosine from D-glucose: olefin cross-metathesis approach. Org. Lett., 7, 5805-5807 (2005).
    • (2005) Org. Lett , vol.7 , pp. 5805-5807
    • Dhavale, D.D.1    Chaudhari, V.D.2    Kumar, K.S.A.3
  • 7
    • 0022974603 scopus 로고
    • Sphingosine inhibition of protein kinase C activity and of phorbol dibutyrate binding in vitro and in human platelets
    • Hannun, Y. A., Loomis, C. R., Merrill, A. H. Jr., and Bell, R. M., Sphingosine inhibition of protein kinase C activity and of phorbol dibutyrate binding in vitro and in human platelets. J. Biol. Chem., 261, 12604-12609 (1986).
    • (1986) J. Biol. Chem , vol.261 , pp. 12604-12609
    • Hannun, Y.A.1    Loomis, C.R.2    Merrill Jr., A.H.3    Bell, R.M.4
  • 9
    • 0037154749 scopus 로고    scopus 로고
    • Highly stereo-selective syntheses of syn- and anti-1,2-amino alcohols
    • Hoffman, R. V., Maslouh, N., and Lee, F. C., Highly stereo-selective syntheses of syn- and anti-1,2-amino alcohols. J. Org. Chem., 67, 1045-1056 (2002).
    • (2002) J. Org. Chem , vol.67 , pp. 1045-1056
    • Hoffman, R.V.1    Maslouh, N.2    Lee, F.C.3
  • 10
    • 27744483875 scopus 로고    scopus 로고
    • Ishikawa, T. and Disadee, W., Chirality transfer from guanidinium ylides to 3-alkenyl (or 3-alkynyl) aziridine-2-carboxylates and application to the syntheses of (2R,3S)-3-hydroxyleucinate and D-erythro- sphingosine. J. Org. Chem., 70, 9399-9406 (2005).
    • Ishikawa, T. and Disadee, W., Chirality transfer from guanidinium ylides to 3-alkenyl (or 3-alkynyl) aziridine-2-carboxylates and application to the syntheses of (2R,3S)-3-hydroxyleucinate and D-erythro- sphingosine. J. Org. Chem., 70, 9399-9406 (2005).
  • 11
    • 33846023340 scopus 로고    scopus 로고
    • Versatile synthetic method for sphingolipids and functionalized sphingosine derivatives via olefin cross metathesis
    • Katsumura, S., Yamamoto, T., Hasegawa, H., and Hakogi, T., Versatile synthetic method for sphingolipids and functionalized sphingosine derivatives via olefin cross metathesis. Org. Lett., 8, 24, 5569-5572 (2006).
    • (2006) Org. Lett , vol.8 , Issue.24 , pp. 5569-5572
    • Katsumura, S.1    Yamamoto, T.2    Hasegawa, H.3    Hakogi, T.4
  • 12
    • 33750465556 scopus 로고    scopus 로고
    • Efficient synthesis of D-erythro-sphingosine and D-erythro-azidosphingosine from D-ribo-phytosphingosine via a cyclic sulfate intermediate
    • Kim, S. H., Lee, S. J., Lee, T. H., Ko, H. J., and Kim, D. J., Efficient synthesis of D-erythro-sphingosine and D-erythro-azidosphingosine from D-ribo-phytosphingosine via a cyclic sulfate intermediate. J. Org. Chem., 71, 8661-8664 (2006).
    • (2006) J. Org. Chem , vol.71 , pp. 8661-8664
    • Kim, S.H.1    Lee, S.J.2    Lee, T.H.3    Ko, H.J.4    Kim, D.J.5
  • 13
    • 3342953528 scopus 로고    scopus 로고
    • Catalytic enantio- and diastereoselective aldol reactions of glycine-derived silicon enolate with aldehydes: An eficient approach to the asymmetric synthesis of anti-β-hydroxy-α-amino acid derivatives
    • Kobayashi, S., Kobayashi, J., Nakamura, M., Mori, Y., and Yamashita, Y., Catalytic enantio- and diastereoselective aldol reactions of glycine-derived silicon enolate with aldehydes: an eficient approach to the asymmetric synthesis of anti-β-hydroxy-α-amino acid derivatives. J. Am. Chem. Soc., 126, 9192-9193 (2004).
    • (2004) J. Am. Chem. Soc , vol.126 , pp. 9192-9193
    • Kobayashi, S.1    Kobayashi, J.2    Nakamura, M.3    Mori, Y.4    Yamashita, Y.5
  • 14
    • 0037034916 scopus 로고    scopus 로고
    • Synthesis of D-erythro-sphingosine and D-erythro-ceramide
    • Kocienski, P. J., Milne, J. E., Jarowicki, K., and Alonso, J., Synthesis of D-erythro-sphingosine and D-erythro-ceramide. Chem. Commun., 426-427 (2002).
    • (2002) Chem. Commun , vol.426-427
    • Kocienski, P.J.1    Milne, J.E.2    Jarowicki, K.3    Alonso, J.4
  • 15
    • 0035920888 scopus 로고    scopus 로고
    • Synthesis of an orthogonally protected D-(+)-erythro-sphingosine
    • Lees, W. J. and Gargano, J. M., Synthesis of an orthogonally protected D-(+)-erythro-sphingosine Tetrahedron Letters, 42, 5845-5847 (2001).
    • (2001) Tetrahedron Letters , vol.42 , pp. 5845-5847
    • Lees, W.J.1    Gargano, J.M.2
  • 16
    • 33744932158 scopus 로고    scopus 로고
    • Enantiodivergent synthesis of D- and L-erythro-sphingosines through Mannich-type reactions of N-benzyl-2,3-O-isopropylidene-D-glyceraldehyde nitrone
    • Merino, P., Jimenez, P., and Tejero, T., Enantiodivergent synthesis of D- and L-erythro-sphingosines through Mannich-type reactions of N-benzyl-2,3-O-isopropylidene-D-glyceraldehyde nitrone. J. Org. Chem., 71, 4685-4688 (2006).
    • (2006) J. Org. Chem , vol.71 , pp. 4685-4688
    • Merino, P.1    Jimenez, P.2    Tejero, T.3
  • 17
    • 35449000202 scopus 로고    scopus 로고
    • Sphingolipids: Metabolism and Cell Signaling
    • Vance, D. E, Vance, J. E, Eds, Elsevier: New York
    • Merrill, A. H., Jr. and Sandhoff, K., Sphingolipids: Metabolism and Cell Signaling. In Biochemistry of Lipids, Lipoprotein, and Membranes; Vance, D. E., Vance, J. E., Eds.; Elsevier: New York, 373-407 (2002).
    • (2002) Biochemistry of Lipids, Lipoprotein, and Membranes , pp. 373-407
    • Merrill Jr., A.H.1    Sandhoff, K.2
  • 19
    • 0032764987 scopus 로고    scopus 로고
    • Synthesis of sphingosine relatives, XXI synthesis of sphingofungin D and its three diastereomers
    • Mori, K. and Otaka, K., Synthesis of sphingosine relatives, XXI synthesis of sphingofungin D and its three diastereomers. Eur. J. Org. Chem., 1999, 1795-1802 (1999).
    • (1999) Eur. J. Org. Chem , vol.1999 , pp. 1795-1802
    • Mori, K.1    Otaka, K.2
  • 20
    • 0037020816 scopus 로고    scopus 로고
    • Efficient stereodivergent synthesis of erythro- and threo-sphingosines: Unprecedented reversal of the stereochemistry in the addition
    • Murakami, T. and Furusawa, K., Efficient stereodivergent synthesis of erythro- and threo-sphingosines: unprecedented reversal of the stereochemistry in the addition. Tetrahedron, 58, 9257-9263 (2002).
    • (2002) Tetrahedron , vol.58 , pp. 9257-9263
    • Murakami, T.1    Furusawa, K.2
  • 21
    • 0041837315 scopus 로고    scopus 로고
    • Raghavan, S. and Rajender, A., Novel, short, stereospecific synthesis of lyxo-(2R,3R,4R)-phytosphingosine and erythro-(2R,3S)-sphingosine. J. Org. Chem., 68, 7094-7097 (2003).
    • Raghavan, S. and Rajender, A., Novel, short, stereospecific synthesis of lyxo-(2R,3R,4R)-phytosphingosine and erythro-(2R,3S)-sphingosine. J. Org. Chem., 68, 7094-7097 (2003).
  • 22
    • 33750630401 scopus 로고    scopus 로고
    • Highly efficient stereoselective synthesis of D-erythro-sphingosine and D-lyxo-phytosphingosine
    • Righi, G., Ciambrone, S., D'Achille C., Leonellia A., and Bonini, C., Highly efficient stereoselective synthesis of D-erythro-sphingosine and D-lyxo-phytosphingosine. Tetrahedron., 62, 11821-11826 (2006).
    • (2006) Tetrahedron , vol.62 , pp. 11821-11826
    • Righi, G.1    Ciambrone, S.2    D'Achille, C.3    Leonellia, A.4    Bonini, C.5
  • 23
    • 0035968851 scopus 로고    scopus 로고
    • Stereoselective synthesis of D-erythro-sphingosine and L-lyxo-phytosphingosine
    • Shiozaki, M. and Nakamura, T., Stereoselective synthesis of D-erythro-sphingosine and L-lyxo-phytosphingosine. Tetrahedron, 57, 9087-9092 (2001).
    • (2001) Tetrahedron , vol.57 , pp. 9087-9092
    • Shiozaki, M.1    Nakamura, T.2
  • 24
    • 0037459676 scopus 로고    scopus 로고
    • Divergent synthesis of D-erythro- sphingosine, L-threo-sphingosine, and their regioisomers
    • Somfai, P. and Olofsson, B., Divergent synthesis of D-erythro- sphingosine, L-threo-sphingosine, and their regioisomers. J. Org. Chem., 68, 2514-2517 (2003).
    • (2003) J. Org. Chem , vol.68 , pp. 2514-2517
    • Somfai, P.1    Olofsson, B.2
  • 25
    • 2942752245 scopus 로고    scopus 로고
    • A practical synthesis of D-erythro-sphingosine using cross-metathesis approach
    • Somfai, P. and Torssell, S., A practical synthesis of D-erythro-sphingosine using cross-metathesis approach. Org. Biomol. Chem., 2, 1643-1646 (2004).
    • (2004) Org. Biomol. Chem , vol.2 , pp. 1643-1646
    • Somfai, P.1    Torssell, S.2
  • 26
    • 85033157393 scopus 로고
    • Synthesis of functionalized prostaglandins via the organozinc-aided three-component method
    • Suzuki, M., Koyano, H., Morita, Y., and Noyori, R., Synthesis of functionalized prostaglandins via the organozinc-aided three-component method. Synlett, 1, 22-23 (1989).
    • (1989) Synlett , vol.1 , pp. 22-23
    • Suzuki, M.1    Koyano, H.2    Morita, Y.3    Noyori, R.4
  • 27
    • 49349137641 scopus 로고
    • A mild, general method for conversion of esters to amides
    • Weinreb, S. M., Basha, A., and Lipton, M., A mild, general method for conversion of esters to amides. Tetrahedron Lett., 18, 4171-4174 (1977).
    • (1977) Tetrahedron Lett , vol.18 , pp. 4171-4174
    • Weinreb, S.M.1    Basha, A.2    Lipton, M.3


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