G
Synthesis
M. Mridha et al.
Paper
(
4) For the early examples of proline-catalyzed direct aldol reac-
tions, see: (a) Hajos, Z. G.; Parrish, D. R. J. Org. Chem. 1974, 39,
(14) (a) Hayashi, Y. Angew. Chem. Int. Ed. 2006, 45, 8103.
(b) Paradowska, J.; Stodulski, M.; Mlynarski, J. Angew. Chem. Int.
Ed. 2009, 48, 4288.
1615. (b) Eder, U.; Sauer, R.; Wiechert, R. Angew. Chem. Int. Ed.
1
971, 10, 496. (c) Pidathala, C.; Hoang, L.; Vignola, N.; List, B.
(15) (a) Kolter, T.; Sandhoff, K. Angew. Chem. Int. Ed. 1999, 38, 1532.
(b) Brodesser, S.; Sawatzki, P.; Kolter, T. Eur. J. Org. Chem. 2003,
2021. (c) Kolter, T. Conformational Restriction of Sphingolipids,
In Highlights Bioorganic Chemistry: Methods and Applications;
Schmuck, C.; Wennemers, H., Eds.; Wiley-VCH: Weinheim,
2004, 48. (d) Liao, J.; Tao, J.; Lin, G.; Liu, D. Tetrahedron 2005, 61,
4715.
Angew. Chem. Int. Ed. 2003, 42, 2785. (d) List, B.; Lerner, R. A.;
Barbas, C. F. III J. Am. Chem. Soc. 2000, 122, 2395.
(
5) (a) Córdova, A.; Zou, W.; Ibrahem, I.; Reyes, E.; Engqvist, M.;
Liao, W.-W. Chem. Commun. 2005, 3586. (b) Córdova, A.; Zou,
W.; Dziedzic, P.; Ibrahem, I.; Reyes, E.; Xu, Y. Chem. Eur. J. 2006,
12, 5383. (c) Dziedzic, P.; Zou, W.; Hafren, J.; Córdova, A. Org.
Biomol. Chem. 2006, 4, 38. (d) Zou, W.; Ibrahem, I.; Dziedzic, P.;
Sunden, H.; Córdova, A. Chem. Commun. 2005, 4946.
(16) (a) Zellner, J. Monatsh. Chem. 1911, 32, 133. (b) Oda, T. J. Pharm.
Soc. Jpn. 1952, 72, 142. (c) Carter, H. E.; Hendrickson, H. S. Bio-
chemistry 1963, 2, 389.
(e) Córdova, A.; Ibrahem, I.; Casas, J.; Sunden, H.; Engqvist, M.;
Reyes, E. Chem. Eur. J. 2005, 11, 4772. For recent reviews of
organocatalysis involving primary amino acid and primary
amines, see: (f) Peng, F.; Shao, Z. J. Mol. Catal. A: Chem. 2008,
(17) (a) Carter, H. E.; Clemer, W. D.; Lands, W. M.; Mullerand, K. L.;
Tomizawa, H. H. J. Biol. Chem. 1954, 206, 613. (b) Kawano, Y.;
Higushi, R.; Isobe, R.; Komori, T. Liebigs Ann. Chem. 1988, 19.
(c) Li, Y.-T.; Hirabayashi, Y.; DeGasperi, R.; Yu, R. K.; Ariga, T.;
Koerner, T. A. W.; Li, S.-C. J. Biol. Chem. 1984, 259, 8980.
(d) Barenholz, Y.; Gatt, S. Biochem. Biophys. Res. Commun. 1967,
27, 319. (e) Amatsu, K. T.; Mikami, M.; Kiguschi, K.; Nozawa, S.;
Iwamori, M. Biochem. Biophys. Acta 1992, 1165, 177. (f) Okabe,
K.; Keenan, R. W.; Schmidt, G. Biochem. Biophys. Res. Commun.
1968, 31, 137. (g) Wertz, P. W.; Miethke, M. C.; Long, S. A.;
Staussand, J. S.; Downing, D. T. J. Invest. Dermatol. 1985, 84, 410.
(h) Vance, D. E.; Sweeley, C. C. Lipid Res. 1967, 8, 621. (i) Dickson,
R. C.; Lester, R. L. Biochim. Biophys. Acta 2003, 1583, 13.
(j) Kobayashi, E.; Motoski, K.; Yamaguchi, Y.; Uchida, T.;
Fukushima, H.; Koezuka, Y. Oncol. Res. 1995, 7, 529.
(18) For recent synthesis of D-lyxo-phytosphingosine, see: (a) Mu, Y.;
Kim, J. Y.; Jin, X.; Park, S. H.; Joo, J. E.; Ham, W. H. Synthesis 2012,
44, 2340. (b) Lee, Y. M.; Baek, D. J.; Lee, S.; Lim, D.; Kim, S. J. Org.
Chem. 2011, 76, 408. (c) Rao, G. S.; Rao, B. V. Tetrahedron Lett.
2011, 52, 6076. (d) Kim, S.; Lee, N.; Lee, S.; Lee, T.; Lee, Y. M.
J. Org. Chem. 2008, 73, 1379. (e) Abraham, E.; Brock, E. A.;
Candela-Lena, J. I.; Davies, S. G.; Georgiou, M.; Nicholson, R. L.;
Perkins, J. H.; Roberts, P. M.; Russell, A. J.; Sánchez-Fernández, E.
M.; Scot, P. M.; Smith, A. D.; Thomson, J. E. Org. Biomol. Chem.
2008, 6, 1665. (f) Righi, G.; Ciambrone, S.; Achille, C. D.; Leonelli,
A.; Bonini, C. Tetrahedron 2006, 62, 11821. For other methods
towards the syntheses of lyxo-phytospingosine and analogues,
see: (g) Dubey, A.; Kumar, P. Tetrahedron Lett. 2009, 50, 3425.
(h) Kumar, I.; Rode, C. V. Tetrahedron: Asymmetry 2007, 18,
1975. (i) Park, J.; Lee, J. H.; Li, Q.; Diaz, K.; Chang, Y. T.; Chung, S.
K. Bioorg. Chem. 2008, 36, 220. (j) Lu, X.; Byun, H. S.; Bittman, R.
J. Org. Chem. 2004, 69, 5433. (k) Tsujimoto, T.; Itoa, Y. Tetrahe-
dron Lett. 2007, 48, 5513.
2
(
1
85, 1. (g) Xu, L.-W.; Luo, J.; Lu, Y. Chem. Commun. 2009, 1807.
h) Tsogoeva, S. B.; Wei, S. Tetrahedron: Asymmetry 2005, 16,
947.
(
6) For pioneering work of using hydrogen bond donor to improve
the stereoselectivity of catalytic aldol reactions by enamine
activation, see: (a) Peelen, T. J.; Chi, Y.; Gellman, S. H. J. Am.
Chem. Soc. 2005, 127, 11598. (b) Zhou, Y.; Shan, Z. J. Org. Chem.
2006, 71, 9510. (c) Chi, Y.; Gellman, S. H. Org. Lett. 2005, 7, 4253.
For a review, see: (d) Companyo, X.; Vicanio, M.; Rios, R. Mini-
Rev. Org. Chem. 2010, 7, 1.
(
7) For examples of primary amino acid-catalyzed syn-selective
direct aldol reaction, see: (a) Wu, X.; Jiang, Z.; Shen, H. M.; Lu, Y.
Adv. Synth. Catal. 2007, 349, 812. (b) Ramasastry, S. S. V.; Zhang,
H.; Tanaka, F.; Barbas, C. F. III J. Am. Chem. Soc. 2007, 129, 288.
(
c) Ramasastry, S. S. V.; Albertshofer, K.; Utsumi, N.; Tanaka, F.;
Barbas, C. F. III Angew. Chem. Int. Ed. 2007, 46, 5572.
d) Ramasastry, S. S. V.; Albertshofer, K.; Utsumi, N.; Barbas, C.
(
F. III Org. Lett. 2008, 10, 1621. (e) Jiang, Z.; Yang, H.; Han, X.; Luo,
J.; Wong, M. W.; Lu, Y. Org. Biomol. Chem. 2010, 8, 1368. (f) Wu,
C.; Fu, X.; Li, S. Eur. J. Org. Chem. 2011, 1291. For examples of
syn-dihydroxyacetone-based organocatalytic aldol reactions,
see: (g) Ref. 7c. (h) Utsumi, N.; Imai, M.; Tanaka, F.; Ramasastry,
S. S. V.; Barbas, C. F. III Org. Lett. 2007, 9, 3445. (i) Markert, M.;
Mulzer, M.; Schetter, B.; Mahrwald, R. J. Am. Chem. Soc. 2007,
129, 7258. (j) Markert, M.; Mahrwald, R. Eur. J. Chem. 2008, 14,
40. (k) Luo, S.; Xu, H.; Zhang, L.; Li, J.; Cheng, J. P. Org. Lett. 2008,
10, 653.
(
8) (a) Lehn, J.-M. Supramolecular Chemistry: Concepts and Perspec-
tives; Wiley-VCH: Weinheim, 1995. (b) Lehn, J.-M. Science 1993,
260, 1762. (c) Lehn, J.-M. Angew. Chem., Int. Ed. Engl. 1990, 29,
1
304.
(19) For recent reviews on the synthesis of phytosphingosines and
analogues, see: (a) Howell, A. R.; Ndakala, A. J. Curr. Org. Chem.
2002, 6, 365; and references cited therein. (b) Liao, J.; Tao, J.; Lin,
D. Tetrahedron 2005, 61, 4715. (c) Morales-Serna, J. A.; Llaveria,
J.; Diaz, Y.; Matheu, M. I.; Castillón, S. Curr. Org. Chem. 2010, 14,
2483; and references cited therein.
(
9) (a) Reis, O.; Eymur, S.; Reis, B.; Demir, A. S. Chem. Commun.
009, 1088. (b) Companyo, X.; Valero, G.; Crovetto, L.; Moyano,
2
A.; Rios, R. Chem. Eur. J. 2009, 15, 6564. (c) Yu, X.; Wang, W.
Chem. Asian J. 2008, 3, 516. (d) Schreiner, P. R. Org. Lett. 2002, 4,
217.
(
(
(
10) Lin, S.; Deiana, L.; Zhao, G.-L.; Sun, J.; Córdova, A. Angew. Chem.
(20) Selected publications for the synthesis of phytosphingosines,
see: (a) Eleuterio, A. S.; Quintero, L.; Piscil, F. S. J. Org. Chem.
2011, 76, 5466. (b) Perali, R. S.; Mandava, S.; Chalapala, S. Tetra-
hedron 2011, 67, 9277. (c) Rao, G. S.; Rao, B. V. Tetrahedron Lett.
2011, 52, 4859. (d) Martinkova, M.; Gonda, J.; Pomikalova, K.;
Kozisek, J.; Kuchar, J. Carbohydr. Res. 2011, 346, 1728.
(e) Ballereau, S.; Abadie, N. A.; Saffon, N.; Génisson, Y. Tetrahe-
dron 2011, 67, 2570. (f) Kumar, P.; Dubey, A.; Puranik, V. G. Org.
Biomol. Chem. 2010, 8, 5074. (g) Liu, Z.; Byun, H. S.; Bittman, R.
J. Org. Chem. 2010, 75, 4356. (h) Raghavan, S.; Krishnaiah, V.
J. Org. Chem. 2010, 75, 748. (i) Reddipalli, G. S.; Venkataiah, M.;
Int. Ed. 2011, 50, 7624.
11) Ma, G.; Bartoszwicz, A.; Ibrahem, I.; Córdova, A. Adv. Synth.
Catal. 2011, 353, 3114.
12) (a) Naryan, S.; Muldoon, J.; Finn, M. G.; Fokin, V. V.; Kolb, H. C.;
Sharpless, K. B. Angew. Chem. Int. Ed. 2005, 44, 3275. (b) Jung, Y.;
Marcus, R. A. J. Am. Chem. Soc. 2007, 129, 5492.
(
13) For reviews discussing factors required to make a reaction in
water environmentally benign, see: (a) Chanda, A.; Fokin, V. V.
Chem. Rev. 2009, 109, 725. (b) Blackmond, D. G.; Armstrong, A.;
Coombe, V.; Wells, A. Angew. Chem. Int. Ed. 2007, 46, 3798.
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Georg Thieme Verlag Stuttgart · New York — Synthesis 2016, 48, A–H