An efficient, stereoselective synthesis of (-)-bulgecinine from (S)-aspartic acid

Tetrahedron Asymmetry

Volumn 8, Issue 12, 1997, Pages 2001-2005

  Fehn, Susanna ^a   Burger, Klaus ^a  

^a UNIVERSITY OF LEIPZIG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ASPARTIC ACID; BULGECININE; GLYCOPEPTIDE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030954456     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(97)00215-2     Document Type: Article

References (30)

1. a) A. Imada, K. Kintaka, M. Nakao, S. Shinagawa, J. Antibiot. 1982, 35, 1400-1403;
2. b) S. Shinagawa, F. Kasahara, Y. Wada, S. Harada, M. Asai, Tetrahedron 1984, 40, 3465-3470;
3. c) S. Shinagawa, M. Maki, K. Kintaka, A. Imada, M. Asai, J. Antibiot. 1985, 38, 17-23.
4. a) T. Wakamiya, K. Yamanoi, M. Nishikawa, T. Shiba, Tetrahedron Lett. 1985, 26, 4759-4760;
5. b) B. P. Bashyal, H.-F. Chow, G. W. J. Fleet, Tetrahedron Lett. 1986, 27, 3205-3208;
6. c) Y. Ohfune, K. Hori, M. Sakaitani, Tetrahedron Lett. 1986, 27, 6079-6082;
7. d) B. P. Bashyal, H.-F. Chow, G. W. J. Fleet, Tetrahedron 1987, 43, 423-430;
8. e) T. Ohta, A. Hosoi, S. Nozoe, Tetrahedron Lett. 1988, 29, 329-332;
9. f) A. G. M. Barrett, D. Pilipauskas, J. Org. Chem. 1990, 55, 5194-5196;
10. g) A. G. M. Barrett, D. Pilipauskas, J. Org. Chem. 1991, 56, 2787-2800;
11. h) Y. Hirai, T. Terada, Y. Amemiya, T. Momose, Tetrahedron Lett. 1992, 33, 7893-7894;
12. i) W. Oppolzer, R. Moretti, C. Zhou, Helv. Chim. Acta 1994, 77, 2363-2380;
13. j) A. Madau, G. Porzi, S. Sandri, Tetrahedron Asymmetry 1996, 7, 825-830;
14. k) S. K. Panday, N. Langlois, Synth. Comm. 1997, 27, 1373-1384.
15. S. Fehn, Dissertation, Technische Universität München, 1995.
16. M. Rudolph, Dissertation, Technische Universität München, 1991.
17. K. Burger, M. Rudolph, Chem-Ztg. 1990, 114, 249-251.
18. K. Burger, M. Rudolph, H. Neuhauser, M. Gold, Synthesis 1992, 1150-1156.
19. a) R. W. Ratcliffe, T. N. Salzmann, B. G. Christensen, Tetrahedron Lett. 1980, 21, 31-34;
20. b) M. P. Doyle, Chem. Rev. 1986, 86, 919-939;
21. c) G. Maas, Top. Curr. Chem. 1987, 137, 75-253;
22. d) J. Adams, D. M. Spero, Tetrahedron 1991, 47, 1765-1808;
23. e) E. Aller, R. T. Buck, M. J. Drysdale, L. Ferris, D. Haigh, C. J. Moody, N. D. Pearson, J. B. Sanghera, J. Chem. Soc. Perkin Trans. 1 1996, 2879-2884.
24. f) F. Zaragoza, Tetrahedron 1997, 53, 3425-3439.
25. K. Burger, M. Rudolph, S. Fehn, Angew. Chem. 1993, 105, 293-295; Angew. Chem. Int. Ed. Engl. 1993, 32, 285-287.
26. K. Burger, M. Rudolph, S. Fehn, Angew. Chem. 1993, 105, 293-295; Angew. Chem. Int. Ed. Engl. 1993, 32, 285-287.
27. Melting points (uncorrected): Tottoli apparatus (Büchi SMP-20) or Boetius hot stage microscope. IR spectra: Perkin-Elmer spectrometers 157 G and 257. NMR: Bruker AM 360/AC 250/AC 200. Elemental analyses: C,H,N analyser EA 415/0, Monar System (Heraeus). Optical rotations: Perkin-Elmer 241 MC polarimeter (Na-D-line). CD spectrometer: Jasco J-715. GC/MS: HP 5890 with coupling to HP 5972 A MSD (Hewlett-Packard) 30 m column HP 5-MS, Mass spectra (EI): Varian MAT CH5 (70 eV). High resolution MS: Fisons VG Autospec. Chromatography: ion-exchange resin (hydrogen form): Amberlite IR-120, 16-45 mesh; flash silica gel (Riedel-de-Haën) 30-63 μm; reversed-phase silica gel (Merck, 60 silanized) 63-200 μm.
28. Trifluoroacetic acid as external standard.
29. 19F NMR.
30. L. Fowden, P. M. Scopes, R. N. Thomas, J. Chem. Soc. (C) 1971, 833-840.