PDF herunterladen
Synthesis 2012(4): 561-568  
DOI: 10.1055/s-0031-1289677
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Chiral Five-, Six-, and Seven-Membered Heterocycles from (S)-3-Hydroxy-γ-butyrolactone

Hao Yang, Navneet Goyal, Jean Rene Ella-Menye, Kristopher Williams, Guijun Wang*
Department of Chemistry, University of New Orleans, New Orleans, LA 70148, USA
Fax: +1(504)2806860; e-Mail: gwang2@uno.edu ;
Weitere Informationen

Publikationsverlauf

Received 26 October 2011
Publikationsdatum:
30. Januar 2012 (online)

    Lizenzen und Reprints Alle Artikel dieser Rubrik

Abstract

Chiral small molecules such as amino alcohols and their heterocyclic derivatives are useful building blocks for asymmetric synthesis and the preparation of biologically active compounds. Using a common starting material derived from carbohydrate, the (S)-3-hydroxy-γ-butyrolactone, we have synthesized several five-, six-, and seven-membered nitrogen-containing chiral heterocycles. These include (S)-3-benzyloxypyrrolidine, a protected 6-substituted morpholin-3-one and its homologous 1,4-oxazepan-3-one, and 6-trityloxymethyl tetrahydro-1,3-oxazine-2-thiones. These chiral small heterocycles were synthesized from the lactone via efficient cyclization reactions. Their syntheses and characterization are reported here.

Key words

amino alcohols - heterocycles - cyclization - lactones - chiral pool - asymmetric synthesis

    References

  • 1 Wang G. Curr. Med. Chem. Anti-infective Agents  2008,  7:  32 
    Google Scholar
  • 2 Geary LM. Hultin PG. Tetrahedron: Asymmetry  2009,  20:  131 
    Google Scholar
  • 3 Sibi MP. Ji J. Wu JH. Guertler S. Porter NA. J. Am. Chem. Soc.  1996,  118:  9200 
    Google Scholar
  • 4 Fedida D, Beatch GN, Ezrin AM, Orth P, and Hesketh C. inventors; PCT Int. Appl. WO 2005018635 A2  20050303.  ; Chem. Abstr. 2005, 142, 274013
  • 5a Sternfeld F. Guiblin AR. Jelley RA. Matassa VG. Reeve AJ. Hunt PA. Beer MS. Heald A. Stanton JA. Sohal B. J. Med. Chem.  1999,  42:  677 
    Google Scholar
  • 5b Baker R, Bourrain S, Castro Pineiro JL, Chambers MS, Guiblin AR, Hobbs SC, Jelley RA, Madin A, and Matassa VG. inventors; PCT A1 Int. Appl. WO 9604274  A1 19960215.  ; Chem. Abstr. 1996, 125, 58520
  • 6 Schohe R, Seidel PR, Traber J, and Glaser T. inventors; Eur. Pat. Appl. EP 338331 A1  19891025.  ; Chem. Abstr. 1989, 112, 235290
  • 7 Chappie TA. Humphrey JM. Allen MP. Estep KG. Fox CB. Lebel LA. Liras S. Marr ES. Menniti FS. Pandit J. Schmidt CJ. Tu M. Williams RD. Yang FV. J. Med. Chem.  2007,  50:  182 
    Google Scholar
  • 8 Lainton JAH. Allen MC. Burton M. Cameron S. Edwards TRG. Harden G. Hogg R. Leung W. Miller S. Morrish JJ. Rooke SM. Wendt B. J. Comb. Chem.  2003,  5:  400 
    Google Scholar
  • 9 Berg S. Larsson L.-G. Renyi L. Ross SB. Thorberg S.-O. Thorell-Svantesson G. J. Med. Chem.  1998,  41:  1934 
    Google Scholar
  • 10 Collins I, Reader JC, Cheung KM, Matthews TP, Proisy N, and Klair SS. inventors; PCT Int. Appl. WO 2008075007 A1  20080626.  ; Chem. Abstr. 2008, 149, 104737
  • 11 Roehrig S. Straub A. Pohlmann J.  Lampe T. Pernerstorfer J. Schlemmer K. Reinemer P. Perzborn E. J. Med. Chem.  2005,  48:  5900 
    Google Scholar
  • 12 Hutchinson DK. Curr. Top. Med. Chem.  2003,  3:  1021 
    Google Scholar
  • 13 Wang G. Ella-Menye J.-R. Sharma V. Bioorg. Med. Chem. Lett.  2006,  16:  2177 
    Google Scholar
  • 14a Claremon DA, Zhuang L, Leftheris K, Tice CM, Ye Y, Singh SB, and Himmelsbach F. inventors; PCT Int. Appl. WO 2009134387 A1  20091105.  ; Chem. Abstr. 2009, 151, 508610
  • 14b Claremon DA, He W, McGeehan G, Singh SB, Tice CM, Xu Z, Ye Y, Zhao W, Zhuang L, and Cacatian S. inventors; PCT Int. Appl. WO 2009017664 A1  20090205.  ; Chem. Abstr. 2009, 150, 214405
  • 15 Fensome A. Bender R. Chopra R. Cohen J. Collins MA. Hudak V. Malakian K. Lockhead S. Olland A. Svenson K. Terefenko EA. Unwalla RJ. Wilhelm J. Wolfrom S. Zhu Y. Winneker RC. Wrobel J. J. Med. Chem.  2005,  48:  5092 
    Google Scholar
  • 16 Zhou H.-B. Lee JH. Mayne CG. Carlson KE. Katzenellenbogen JA. J. Med. Chem.  2010,  53:  3349 
    Google Scholar
  • 17a Lim C.-W, Boo CJ, Kim KH, and Kim S.-J. inventors; PCT Int. Appl.; WO 2007024113 A1  20070301.  ; Chem. Abstr. 2007, 146, 274214
  • 17b Kocalka P. Pohl R. Rejman D. Rosenberg I. Tetrahedron  2006,  62:  5763 
    Google Scholar
  • 18 Plouvier BMC, Chou DTH, Jung G, Choi LSL, Sheng T, Barrett AGM, Passafaro MS, Kurz M, Moeckli D, and Ulmann P. inventors; PCT Int. Appl. WO 2006088525 A1  20060824.  ; Chem. Abstr. 2006, 145, 271413
  • 19 Chen Z. Chen Z. Jiang Y. Hu W. Synlett  2004,  1763 
    Google Scholar
  • 20 Beatch GN, Choi LSL, Jung G, Liu Y, Plouvier B, Wall R, Zhu J, Zolotoy A, and Barrett AGM. inventors; PCT Int. Appl. WO 2004099137 A1  20041118.  ; Chem. Abstr. 2004, 141, 424107
  • 21 Brenner E. Baldwin RM. Tamagnan G. Org. Lett.  2005,  7:  937 
    Google Scholar
  • 22 Tamagnan GD, and Alagille D. inventors; PCT Int. Appl. WO 2007005935 A2  20070111.  ; Chem. Abstr. 2007, 146, 121754
  • 23 Henegar KE. J. Org. Chem.  2008,  73:  3662 
    Google Scholar
  • 24 Barta NS, Glase SA, Gray DL, Reichard GA, Simons LJ, and Xu W. inventors; US Pat. Appl. Publ. US 20050245519 A1  20051103.  ; Chem. Abstr. 2005, 143, 440426
  • 25 Kojima T. Niigata K. Fujikura T. Tachikawa S. Nozaki Y. Kagami S. Takahashi K. Chem. Pharm. Bull.  1985,  33:  3766 
    Google Scholar
  • 26 Ella-Menye J.-R. Wang G. Tetrahedron  2007,  63:  10034 
    Google Scholar
  • 27 Ella-Menye J.-R. Sharma V. Wang G. J. Org. Chem.  2005,  70:  463 
    Google Scholar
  • 28 Davies SG. Fletcher AM. Kurosawa W. Lee JA. Poce G. Roberts PM. Thomson JE. Williamson DM. J. Org. Chem.  2010,  75:  7745 
    Google Scholar
  • 29 Zhang P, and Kern J. inventors; US Pat. Appl. Publ. US 20050085470 A1  20050421.  ; Chem. Abstr. 2005, 142, 411364
  • 30 Higuchi RI, Zhi L, Adams ME, Liu Y, and Karanewsky DS. inventors; PCT Int. Appl. WO  2006010142.  ; Chem. Abstr. 2006, 144, 171000
  • 31 Kobayashi K. Yokoi Y. Komatsu T. Konishi H. Tetrahedron  2010,  66:  9336 
    Google Scholar
  • 32 Li G. Ohtani T. Heterocycles  1997,  45:  2471 
    Google Scholar
  • 33 Hollingsworth RI. Wang G. Chem. Rev.  2000,  100:  4267 
    Google Scholar
  • 34 Wang G. Hollingsworth RI. Tetrahedron: Asymmetry  2000,  11:  4429 
    Google Scholar
  • 35 Wang G. Hollingsworth RI. J. Org. Chem.  1999,  64:  1036 
    Google Scholar
  • 36 Ahn M. Pietersma AL. Schofield LR. Parker EJ. Org. Biomol. Chem.  2005,  3:  4046 
    Google Scholar
  • 37 Takeda T, Ohnuki M, and Kishimoto N. inventors; PCT Int. Appl.  WO 2007023824 A1 20070301.  ; Chem. Abstr. 2008, 146, 295766