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

doi:10.1055/s-0031-1289677

PAPER

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 ;

Abstract

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

Volltext

Referenzen

References

1 Wang G. Curr. Med. Chem. Anti-infective Agents 2008, 7: 32

2 Geary LM. Hultin PG. Tetrahedron: Asymmetry 2009, 20: 131

3 Sibi MP. Ji J. Wu JH. Guertler S. Porter NA. J. Am. Chem. Soc. 1996, 118: 9200

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

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

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

9 Berg S. Larsson L.-G. Renyi L. Ross SB. Thorberg S.-O. Thorell-Svantesson G. J. Med. Chem. 1998, 41: 1934

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

12 Hutchinson DK. Curr. Top. Med. Chem. 2003, 3: 1021

13 Wang G. Ella-Menye J.-R. Sharma V. Bioorg. Med. Chem. Lett. 2006, 16: 2177

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

16 Zhou H.-B. Lee JH. Mayne CG. Carlson KE. Katzenellenbogen JA. J. Med. Chem. 2010, 53: 3349

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

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

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

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

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

26 Ella-Menye J.-R. Wang G. Tetrahedron 2007, 63: 10034

27 Ella-Menye J.-R. Sharma V. Wang G. J. Org. Chem. 2005, 70: 463

28 Davies SG. Fletcher AM. Kurosawa W. Lee JA. Poce G. Roberts PM. Thomson JE. Williamson DM. J. Org. Chem. 2010, 75: 7745

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

32 Li G. Ohtani T. Heterocycles 1997, 45: 2471

33 Hollingsworth RI. Wang G. Chem. Rev. 2000, 100: 4267

34 Wang G. Hollingsworth RI. Tetrahedron: Asymmetry 2000, 11: 4429

35 Wang G. Hollingsworth RI. J. Org. Chem. 1999, 64: 1036

36 Ahn M. Pietersma AL. Schofield LR. Parker EJ. Org. Biomol. Chem. 2005, 3: 4046

37 Takeda T, Ohnuki M, and Kishimoto N. inventors; PCT Int. Appl. WO 2007023824 A1 20070301. ; Chem. Abstr. 2008, 146, 295766

Zusatzmaterial

Supporting Information