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Synthesis 2007(21): 3399-3405  
DOI: 10.1055/s-2007-990802
PAPER
© Georg Thieme Verlag Stuttgart · New York

New Synthetic Routes toward Enantiopure (2S,3R,4R)-4-Hydroxyisoleucine by 1,3-Dipolar Cycloaddition of a Chiral Nitrone to C4 Alkenes

Kaiss Aouadia,b, Erwann Jeanneauc, Moncef Msaddekb, Jean-Pierre Praly*a
a Institut de Chimie et Biochimie Moléculaires et Supramoléculaires (ICBMS), CNRS, UMR5246, Université Lyon 1, CPE Lyon, bâtiment 308, 43 boulevard du 11 Novembre 1918, F-69622 Villeurbanne, France
Fax: +33(4)72448349; e-Mail: jean-pierre.praly@univ-lyon1.fr;
b Laboratoire de Synthèse Hétérocyclique, Chimie des Substances Naturelles, Faculté des Sciences de Monastir, Université de Monastir, 5019 Monastir, Tunisia
c Centre de Diffractométrie Henri Longchambon, Université Lyon 1, Bât. Raulin, 43 Boulevard du 11 Novembre 1918, 69622 Villeurbanne, France
Further Information

Publication History

Received 12 June 2007
Publication Date:
16 October 2007 (online)

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Abstract

1,3-Dipolar cycloaddition reaction of a chiral nitrone derived from (-)-menthone to E/Z mixtures of crotonaldehyde or (Z)-but-2-en-1,4-diol opens, by simultaneous creation of three contiguous asymmetric centers, new access to enantiopure (2S,3R,4R)-4-hydroxyisoleucine, respectively in 13% (7 steps) and 34% (6 steps) overall yield.

Key words

chiral nitrone - 1,3-dipolar cycloaddition - isoxazolidines - stereocontrol - 4-hydroxyisoleucine

    References

  • 1 Ross SA. Gulve EA. Chem. Rev.  2004,  104:  1255 
    CrossrefGoogle Scholar
  • 2 Nagy V. PhD Thesis   University of Debrecen; Hungary: 2003. 
    Google Scholar
  • 3 Oikonomakos NG. Kosmopoulou M. Zographos SE. Leonidas DD. Chrysina ED. Somsák L. Nagy V. Praly J.-P. Docsa T. Tóth B. Gergely P. Eur. J. Biochem.  2002,  269:  1684 
    CrossrefGoogle Scholar
  • 4 Benltifa M. Vidal S. Fenet B. Msaddek M. Goekjian PG. Praly J.-P. Brunyánszki A. Docsa T. Gergely P. Eur. J. Org. Chem.  2006,  4242 
    CrossrefGoogle Scholar
  • 5 Benltifa M. Vidal S. Gueyrard D. Goekjian PG. Msaddek M. Praly J.-P. Tetrahedron Lett.  2006,  47:  6143 
    CrossrefGoogle Scholar
  • 6 He L. Zhang Y.-Z. Tanoh M. Chen G.-R. Praly J.-P. Chrysina ED. Tiraidis C. Kosmopoulou M. Leonidas DD. Oikonomakos NG. Eur. J. Org. Chem.  2007,  596 
    CrossrefGoogle Scholar
  • 7a Oikonomakos NG. Curr. Protein Pept. Sci.  2002,  3:  561 
    CrossrefGoogle Scholar
  • 7b Somsák L. Nagy V. Hadady Z. Docsa T. Gergely P. Curr. Pharm. Des.  2003,  9:  1177 
    CrossrefGoogle Scholar
  • 7c Somsák L. Nagy V. Hadady Z. Felföldi N. Docsa T. Gergely P. In Frontiers in Medicinal Chemistry   Vol. 2:  Reitz AB. Kordik CP. Choudhary MI. . Bentham Science Publishers; Hilversum, The Netherlands: 2005.  p.253 
    CrossrefGoogle Scholar
  • 8a Nasi R. Sim L. Rose DR. Pinto MB. J. Org. Chem.  2007,  72:  180 ; and references cited therein
    CrossrefGoogle Scholar
  • 8b Tanabe G. Yoshikai K. Hatanaka T. Yamamoto M. Shao Y. Minematsu T. Muraoka O. Wang T. Matsuda H. Yoshikawa M. Bioorg. Med. Chem.  2007,  15:  3926 ; and references cited therein
    CrossrefGoogle Scholar
  • 9 Sauvaire Y. Petit P. Broca C. Manteghetti M. Baissac Y. Fernandez-Alvarez J. Gross R. Roye M. Leconte A. Gomis R. Ribes G. Diabetes  1998,  47:  206 
    CrossrefGoogle Scholar
  • 10a Wieland T. Wehrt H. Justus Liebigs Ann. Chem.  1966,  700:  120 
    CrossrefGoogle Scholar
  • 10b Wieland T. Hasan M. Pfaender P. Justus Liebigs Ann. Chem.  1968,  717:  205 
    CrossrefGoogle Scholar
  • 10c Wieland T. Fahrmeir A. Justus Liebigs Ann. Chem.  1970,  736:  95 
    CrossrefGoogle Scholar
  • 10d Gieren A. Narayanan P. Hoppe W. Hasan M. Michl K. Wieland T. Smith HO. Jung G. Breitmaier E. Justus Liebigs Ann. Chem.  1974,  1561 
    CrossrefGoogle Scholar
  • 10e Hasan M. Georgopoulos D. Wieland T. Justus Liebigs Ann. Chem.  1976,  781 
    CrossrefGoogle Scholar
  • 11a Fowden L. Pratt HM. Smith A. Phytochemistry  1973,  12:  1707 
    CrossrefGoogle Scholar
  • 11b Alcock NW. Crout DHG. Gregorio MVM. Lee E. Pike G. Samuel CJ. Phytochemistry  1989,  28:  1835 
    CrossrefGoogle Scholar
  • 12a Sauvaire Y. Girardon P. Baccou JC. Ristérucci AM. Phytochemistry  1984,  23:  479 
    CrossrefGoogle Scholar
  • 12b Broca C. Gross R. Petit P. Sauvaire Y. Manteghetti M. Tournier M. Maseillo P. Gomis R. Ribes G. Am. J. Physiol. Endocrinol. Metab.  1999,  277:  E617 
    CrossrefGoogle Scholar
  • 12c Broca C. Manteghetti M. Gross R. Baissac Y. Jacob M. Petit P. Sauvaire Y. Ribes G. Eur. J. Pharmacol.  2000,  390:  339 
    CrossrefGoogle Scholar
  • 12d Broca C. Breil V. Cruciani-Guglielmacci C. Manteghetti M. Rouault C. Derouet M. Rizkalla S. Pau B. Petit P. Ribes G. Ktorza A. Gross R. Reach G. Taouis M. Am. J. Physiol. Endocrinol. Metab.  2004,  287:  E463 
    CrossrefGoogle Scholar
  • 13 Narender T. Puri A. . Khaliq T. Saxena R. Bhatia G. Chandra R. Bioorg. Med. Chem. Lett.  2006,  16:  293 
    CrossrefGoogle Scholar
  • 14a Potier P, Ouazzani J, Rodelet J.-F, Sasaki NA, and Zhu WQ. inventors; European Patent  1495753.  ; Chem. Abstr. 2004, 142, 62343
  • 14b Dal Farra C, Domloge N, and Peyronel D. inventors; European Patent  1620185.  ; Chem. Abstr. 2004, 141, 319491
  • 14c Dal Farra C, Domloge N, and Peyronel D. inventors; French Patent  2887773.  ; Chem. Abstr. 2007, 146, 128031
  • 15 Gull R. Schöllkopf U. Synthesis  1985,  1052 
    Article in Thieme ConnectGoogle Scholar
  • 16 Inghardt T. Fredj G. Svensson G. Tetrahedron  1991,  47:  6469 
    CrossrefGoogle Scholar
  • 17 Kassem T. Wehbe J. Rolland-Fulcrand V. Rolland M. Roumestant M.-L. Martinez J. Tetrahedron: Asymmetry  2001,  12:  2657 
    CrossrefGoogle Scholar
  • 18 Rolland-Fulcrand V. Rolland M. Roumestant ML. Martinez J. Eur. J. Org. Chem.  2004,  873 
    CrossrefGoogle Scholar
  • 19a Ouazzani J, Potier P, Sasaki NA, and Wang Q. inventors; European Patent  1268397.  ; Chem. Abstr. 2001, 135, 273168
  • 19b Wang Q. Ouazzani J. Sasaki NA. Potier P. Eur. J. Org. Chem.  2002,  834 
    Google Scholar
  • 20a Jamieson AG. Sutherland A. Willis CL. Org. Biomol. Chem.  2004,  2:  808 
    CrossrefGoogle Scholar
  • 20b For a related racemic synthesis, see: Dong Y. Pai NN. Ablaza SL. Yu S.-X. Bolvig S. Forsyth DA. Le Quesne PW. J. Org. Chem.  1999,  64:  2657 
    CrossrefGoogle Scholar
  • 21a Becht J.-M. De Lamo Marin S. Maruani M. Wagner A. Mioskowski C. Tetrahedron  2006,  62:  4430 
    CrossrefGoogle Scholar
  • 21b Mioskowski C, Wagner A, De Lamo MS, Catala C, and Becht JM. inventors; European Patent  1572623.  ; Chem. Abstr. 2004, 141, 23901
    Crossref
  • 21c Mioskowski C, Wagner A, and Catala C. inventors; European Patent  1620390.  ; Chem. Abstr. 2004, 141, 395803
    Crossref
  • 21d Mioskowski C, and Wagner A. inventors; European Patent  1657236.  ; Chem. Abstr. 2006, 144, 433106
    Crossref
  • 22 Aouadi K. Vidal S. Msaddek M. Praly J.-P. Synlett  2006,  3299 
    Article in Thieme ConnectGoogle Scholar
  • 23 Revuelta J. Cicchi S. Goti A. Brandi A. Synthesis  2007,  485 
    Article in Thieme ConnectGoogle Scholar
  • 24a Katagiri N. Okada M. Morishita Y. Kaneko C. Tetrahedron  1997,  53:  5725 
    CrossrefGoogle Scholar
  • 24b Vogt A, Altenbach H.-J, Kirschbaum M, Hahn MG, Matthäus MSP, and Hermann AR. inventors; European Patent  976721.  ; Chem. Abstr. 2000, 132, 108296
    Crossref
  • 24c Westermann B. Walter A. Flörke U. Altenbach H.-J. Org. Lett.  2001,  3:  1375 
    CrossrefGoogle Scholar
  • 26 Gottlieb HE. Kotlyar V. Nudelman A. J. Org. Chem.  1997,  62:  7512 
    CrossrefPubMedGoogle Scholar
25

Crystal data of compound (4R)-6: C17H29IN2O2, M = 420.33, orthorhombic, P212121, a = 8.761(5) Å, b = 10.744(5) Å, c = 20.202(5) Å, V = 1901.6(18) Å3, Z = 4, D x = 1.468 Mg m-3, µ (Mo-Kα) = 1.69 mm-1, F(000) = 856, colorless block, 0.05 × 0.05 × 0.05 mm, 4201 reflections measured (R int = 0.000), 4183 unique, wR 2 = 0.040, conventional R = 0.032 on F values of 3704 reflections with I > 2.0 σ(I), (Δ/σ)max = 0.001), S = 1.06 for all data and 200 parameters. Unit cell determination and intensity data collection (θmax = 27.83°) were performed on a Nonius KappaCCD at 293 (2) K. Structure solutions were found by direct methods and refinements were achieved by full-matrix least-squares methods on F. Further details of the crystal structure investigation can be obtained from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK (CCDC deposition no. 641986).
Crystal data of compound 11: C17H28I2N2O2, M = 546.23, orthorhombic, P212121, a = 8.116(5) Å, b = 8.878(5) Å, c = 28.745(5) Å, V = 2071.2(18) Å3, Z = 4, D x = 1.752 Mg m-3, µ (Mo-Kα) = 3.05 mm-1, F(000) = 1064, colorless prism, 0.39 × 0.25 × 0.23 mm, 9967 reflections measured (R int = 0.095), 4488 unique, wR 2 = 0.052, conventional R = 0.045 on F values of 2322 reflections with I > 2.0 σ(I), (Δ/σ)max = 0.001), S = 1.12 for all data and 209 parameters. Unit cell determination and intensity data collection (θmax = 27.83°) were performed on a Nonius KappaCCD at 293 (2) K. Further details of the crystal structure investigation can be obtained from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK (CCDC deposition no. 641985).