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

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 
• 2 Nagy V. PhD Thesis   University of Debrecen; Hungary: 2003. 
• 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 
• 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 
• 5 Benltifa M. Vidal S. Gueyrard D. Goekjian PG. Msaddek M. Praly J.-P. Tetrahedron Lett.  2006,  47:  6143 
• 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 
• 7a Oikonomakos NG. Curr. Protein Pept. Sci.  2002,  3:  561 
• 7b Somsák L. Nagy V. Hadady Z. Docsa T. Gergely P. Curr. Pharm. Des.  2003,  9:  1177 
• 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 
• 8a Nasi R. Sim L. Rose DR. Pinto MB. J. Org. Chem.  2007,  72:  180 ; and references cited therein
• 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
• 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 
• 10a Wieland T. Wehrt H. Justus Liebigs Ann. Chem.  1966,  700:  120 
• 10b Wieland T. Hasan M. Pfaender P. Justus Liebigs Ann. Chem.  1968,  717:  205 
• 10c Wieland T. Fahrmeir A. Justus Liebigs Ann. Chem.  1970,  736:  95 
• 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 
• 10e Hasan M. Georgopoulos D. Wieland T. Justus Liebigs Ann. Chem.  1976,  781 
• 11a Fowden L. Pratt HM. Smith A. Phytochemistry  1973,  12:  1707 
• 11b Alcock NW. Crout DHG. Gregorio MVM. Lee E. Pike G. Samuel CJ. Phytochemistry  1989,  28:  1835 
• 12a Sauvaire Y. Girardon P. Baccou JC. Ristérucci AM. Phytochemistry  1984,  23:  479 
• 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 
• 12c Broca C. Manteghetti M. Gross R. Baissac Y. Jacob M. Petit P. Sauvaire Y. Ribes G. Eur. J. Pharmacol.  2000,  390:  339 
• 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 
• 13 Narender T. Puri A. . Khaliq T. Saxena R. Bhatia G. Chandra R. Bioorg. Med. Chem. Lett.  2006,  16:  293 
• 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 
• 16 Inghardt T. Fredj G. Svensson G. Tetrahedron  1991,  47:  6469 
• 17 Kassem T. Wehbe J. Rolland-Fulcrand V. Rolland M. Roumestant M.-L. Martinez J. Tetrahedron: Asymmetry  2001,  12:  2657 
• 18 Rolland-Fulcrand V. Rolland M. Roumestant ML. Martinez J. Eur. J. Org. Chem.  2004,  873 
• 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 
• 20a Jamieson AG. Sutherland A. Willis CL. Org. Biomol. Chem.  2004,  2:  808 
• 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 
• 21a Becht J.-M. De Lamo Marin S. Maruani M. Wagner A. Mioskowski C. Tetrahedron  2006,  62:  4430 
• 21b Mioskowski C, Wagner A, De Lamo MS, Catala C, and Becht JM. inventors; European Patent  1572623.  ; Chem. Abstr. 2004, 141, 23901
• 21c Mioskowski C, Wagner A, and Catala C. inventors; European Patent  1620390.  ; Chem. Abstr. 2004, 141, 395803
• 21d Mioskowski C, and Wagner A. inventors; European Patent  1657236.  ; Chem. Abstr. 2006, 144, 433106
• 22 Aouadi K. Vidal S. Msaddek M. Praly J.-P. Synlett  2006,  3299 
• 23 Revuelta J. Cicchi S. Goti A. Brandi A. Synthesis  2007,  485 
• 24a Katagiri N. Okada M. Morishita Y. Kaneko C. Tetrahedron  1997,  53:  5725 
• 24b Vogt A, Altenbach H.-J, Kirschbaum M, Hahn MG, Matthäus MSP, and Hermann AR. inventors; European Patent  976721.  ; Chem. Abstr. 2000, 132, 108296
• 24c Westermann B. Walter A. Flörke U. Altenbach H.-J. Org. Lett.  2001,  3:  1375 
• 26 Gottlieb HE. Kotlyar V. Nudelman A. J. Org. Chem.  1997,  62:  7512 

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) ų, Z = 4, D _x = 1.468 Mg m^-3, µ (Mo-K_α) = 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 (θ_max = 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) ų, Z = 4, D _x = 1.752 Mg m^-3, µ (Mo-K_α) = 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 (θ_max = 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).