A concise and efficient route to the Alzheimer's therapeutic agent (R)-arundic acid

Tetrahedron

Volumn 64, Issue 47, 2008, Pages 10664-10669

  García, Jesús M ^a   Odriozola, José M ^a   Lecumberri, Ainara ^a   Razkin, Jesús ^a   González, Alberto ^a  

^a PUBLIC UNIVERSITY OF NAVARRE   (Spain)

Author keywords

Alzheimer; Asymmetric alkylation; Camphor; Chiral auxiliary; Diastereoselective

Indexed keywords

2 ENDO [PROPYLOCT 4 ENOYL] 1,7,7 TRIMETHYLBICYCLO[2.2.1]HEPTAN 2 OL; 2 ENDO [PROPYLOCTANOYL] 1,7,7 TRIMETHYLBICYCLO[2.2.1]HEPTAN 2 OL; 2 ENDO ACETYL 1,7,7 TRIMETHYLBICYCLO[2.2.1]HEPTAN 2 OL; 2 ENDO ACETYL 2 EXO TRIMETHYLSILYLOXY 1,7,7 TRIMETHYLBICYCLO[2.2.1]HEPTANE; 2 ENDO OCTANOYL 1,7,7 TRIMETHYLBICYCLO[2.2.1]HEPTAN 2 OL; 2 ENDO PENTANOYL 1,7,7 TRIMETHYLBICYCLO[2.2.1]HEPTAN 2 OL; 2 ENDO PENTANOYL 2 EXO TRIMETHYLSILYLOXY 1,7,7 TRIMETHYLBICYCLO[2.2.1]HEPTANE; 2 EXO TRIMETHYLSILYLOXY 1,7,7 TRIMETHYLBICYCLO[2.2.1]HEPTANE 2 CARBONITRILE; ACETYLENE; ARUNDIC ACID; CAMPHOR; HALIDE; UNCLASSIFIED DRUG;

ALZHEIMER DISEASE; ARTICLE; CARBON SOURCE; CHIRALITY; ENANTIOMER; PRIORITY JOURNAL; SYNTHESIS;

DRYOBALANOPS;

EID: 53149108541     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.09.026     Document Type: Article

References (40)

1. Liuzzi F.J., and Lasek R.J. Science 237 (1987) 642-645
2. Uchida Y., and Tomonaga M. Brain Res. 481 (1989) 190-193
3. Moundijian A., Antel J.P., and Yong V.W. Brain Res. 547 (1991) 223-228
4. Sorbera L.A., Castañer J., and Castañer R.M. Drugs Future 29 (2004) 441-448
5. Tateishi, N.; Ohno, H.; Kishimoto, K.; Ohuchida, S. Japan Patent 7-316092, 1995;
6. Chem. Abstr. 122 (1995) 160096b
7. Tateishi N., Mori T., Kagamiishi Y., Satoh S., Katsube N., Morikawa E., Morimoto T., Matsui T., and Asano T. J. Cereb. Blood Flow Metab. 22 (2002) 723-734
8. Matsui T., Mori T., Tateishi N., Kagamiishi Y., Satoh S., Katsube N., Morikawa E., Morimoto T., Ikuta F., and Asano T. J. Cereb. Blood Flow Metab. 22 (2002) 711-722
9. Lambert C., Utimoto K., and Nozaki H. Tetrahedron Lett. 25 (1984) 5323-5326
10. Kishimoto, K.; Nakai, H. Japan Patent 7-98328, 1995;
11. Chem. Abstr. 126 (1997) 74487
12. Kishimoto, K.; Nakai, H. Japan Patent 7-102693, 1995;
13. Chem. Abstr. 126 (1997) 74488
14. Evans D.A., and Takacs J.M. Tetrahedron Lett. 21 (1980) 4233-4236
15. Sonnet P.E., and Heath R.R. J. Org. Chem. 45 (1980) 3137-3139
16. Hasegawa T., and Yamamoto H. Bull. Chem. Soc. Jpn. 73 (2000) 423-428
17. Hasegawa T., Kawanaka Y., Kasamatsu E., Iguchi Y., Yonekawa Y., Okamoto M., Ohta C., Hashimoto S., and Ohuchida S. Org. Process Res. Dev. 7 (2003) 168-171
18. Oppolzer W., Moretti R., and Thomi S. Tetrahedron Lett. 30 (1989) 5603-5606
19. Oppolzer W., Rosset S., and Brabander J.De. Tetrahedron Lett. 38 (1997) 1539-1540
20. Hasegawa T., and Yamamoto H. Synthesis 8 (2003) 1181-1186
21. Peotier B., Holmes T., and Piva O. Tetrahedron: Asymmetry 16 (2005) 1513-1520
22. Hasegawa T., Kawanaka Y., Kasamatsu E., Ohta C., Nakabayashi K., Okamoto M., Hamano M., Takahashi K., Ohuchida S., and Hamada Y. Org. Process Res. Dev. 9 (2005) 774-781
23. Tokunaga M., Larrow J.F., Kakiuchi F., and Jacobsen E.N. Science 277 (1997) 936-938
24. Goswam D., and Chattopadhyay A. Lett. Org. Chem. 12 (2006) 922-925
25. For reviews, see:
26. Rück K. Angew. Chem., Int. Ed. Engl. 34 (1995) 433-435
27. Franklin A.S. J. Chem. Soc., Perkin Trans. 1 (1998) 2451-2465
28. Regan A.C. J. Chem. Soc., Perkin Trans. 1 (1998) 1151-1166
29. Regan A.C. J. Chem. Soc., Perkin Trans. 1 (1999) 357-373
30. Fey P. In: Helmchen G., Hoffmann R.W., Mulzer J., and Schaumann E. (Eds). Stereoselective Synthesis (Houben-Weyl) E21 Vol. 2 (1996), Georg Thieme, Stuttgart, New York, NY
31. Evans D.A., Dow R.L., Shih T.L., Takacs J.M., and Zhaler R. J. Am. Chem. Soc. 112 (1990) 5290-5313
32. Myers A.G., Yang B.H., Chen H., McKinstry L., Kopecky D.J., and Gleason J.L. J. Am. Chem. Soc. 119 (1997) 6496-6511
33. Backes B.J., Dragoli D.R., and Ellman J.A. J. Org. Chem. 64 (1999) 5472-5478
34. Tessier A., Pytkowicz J., and Brigaud T. Angew. Chem., Int. Ed. 45 (2006) 3677-3681
35. Palomo C., Oiarbide M., Mielgo A., González A., García J.M., Landa C., Lecumberri A., and Linden A. Org. Lett. 3 (2001) 3249-3252
36. Palomo C., González A., García J.M., Landa C., Oiarbide M., Rodríguez S., and Linden A. Angew. Chem., Int. Ed. 37 (1998) 180-182
37. Palomo C., Oiarbide M., Aizpurua J.M., González A., García J.M., Landa C., Odriozola I., and Linden A. J. Org. Chem. 64 (1999) 8193-8200
38. Adapted from. Wilkinson H.S., Grover P.T., Vandenbossche P., Bakale R.P., Bhongle N.N., Wald S.A., and Senanayake C.H. Org. Lett. 3 (2001) 553-556
39. Adapted from. Hung S.-C., Wen Y.-F., Chang J.-W., Liao C.-C., and Uang B.-J. J. Org. Chem. 67 (2002) 1308-1313
40. 25 +41.8 (c 1.0, EtOH).