Monocarbamates, derived from (S)-2-(dibenzylamino)butane-1,4-diol, and the influence of the second O-protecting group on the regioselectivity of deprotonation - Application to the synthesis of the boletus toxin (2S,4S)-γ-hydroxy-norvaline

Synthesis

Volumn , Issue 9, 1998, Pages 1287-1297

  Sendzik, Martin ^a   Guarnieri, Walter ^a   Hoppe, Dieter ^a  

^a UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

( ) sparteine; Chiral aminodiols; Chiral carbamate; Directed lithiation; Stereoselective lithiation

Indexed keywords

MYCOTOXIN;

ARTICLE; DRUG SYNTHESIS; ENANTIOMER; IN VITRO STUDY; INFRARED SPECTROPHOTOMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0031656762     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-6100     Document Type: Article

References (44)

1. Guarnieri, W.; Sendzik, M.; Fröhlich, R.; Hoppe, D. Synthesis, 1998, 1274.
2. Hoppe, D.; Paetow, M.; Hintze, F. Angew. Chem. 1993, 105, 430;
3. Angew. Chem., Int. Ed. Engl. 1993, 32, 394.
4. Reviews: (a) Hoppe, D.; Hense, T. Angew. Chem. 1997, 109, 2376;
5. Angew. Chem. Int. Ed. Engl. 1997, 36, 2282.
6. (b) Hoppe, D.; Hintze, F.; Tebben, P.; Paetow, M.; Ahrens, H.; Schwerdtfeger, J.; Sommerfeld, P.; Haller, J.; Guarnieri, W.; Kolczewski, S.; Hense, T.; Hoppe, I. Pure Appl. Chem. 1994, 66, 1479.
7. Hoppe, D.; Ahrens, H.; Guarnieri, W.; Helmke, H.; Kolczewski, S. Pure Appl. Chem. 1996, 68, 613.
8. Beak, P.; Basu, A.; Gallagher, D. J.; Park, Y. S.; Thayumanavan, S. Acc. Chem. Res. 1996, 29, 552.
9. 1 has independently been prepared, see: (a) Gmeiner, P.; Kärtner, A.; Junge, D. Tetrahedron Lett. 1993, 34, 4325.
10. (b) Gmeiner, P.; Junge, D.; Kärtner, A. J. Org. Chem. 1994, 59, 6766.
11. (a) Albert, R.; Denklmaier, J.; Hönig, H.; Kandolf, H. Synthesis 1987, 635.
12. (b) Gmeiner, P.; Feldman, P. L.; Chu-Moyer, M. Y.; Rapoport, H. J. Org. Chem. 1990, 55, 3068.
13. (c) Chevallet, P.; Garrouste, P.; Malawska, B.; Martinez, J. Tetrahedron Lett. 1993, 34, 7409.
14. (d) Burger, K. Chem.-Ztg. 1990, 114, 249.
15. (e) Winkler, D.; Burger, K. Synthesis 1996, 1419.
16. (f) Stein, K. A.; Toogood. P. L. J. Org. Chem. 1995, 60, 8110.
17. (g) Baldwin, J. E.; North, M.; Flinn, A. Tetrahedron Lett. 1987, 28, 3167.
18. (h) Baldwin, J. E.; North, M.; Flinn, A. Tetrahedron 1988, 44, 637.
19. (i) Cooper, R. D. G.; Jose, F.; McShane, L.; Koppel, G. A. Tetrahedron Lett. 1978, 2243.
20. (j) Jefford, C. W.; Wang J. B.; Lu, Z.-H. Tetrahedron Lett. 1993, 34, 7557.
21. (k) McGarvey, G. J.; Williams, J. M.; Hiner, R. N.; Matsubara, Y.; Oh, T. J. Am. Chem. Soc. 1986, 108, 4943
22. Reetz, M. T.; Schmitz, A.; Holdgrün, X. Tetrahedron Lett. 1989, 30, 5421.
23. Gmeiner, P. Arch. Pharm. (Weinheim) 1991, 324, 551.
24. The costs according to Aldrich in 1996/1997 are DM 18.60/ 100 g for (S)-aspartic acid, DM 64.60/100 g for (S)-asparagine, and DM 143.20/100 g for (S)-homoserine.
25. Guarnieri, W. Diploma Thesis, Universität Kiel 1992.
26. Hintze, F.; Hoppe, D. Synthesis 1992, 1216.
27. Brown, H. C.; Kim S. C. Synthesis 1977, 635.
28. 1H NMR spectroscopy after reacting with (-)-(R)-α-methoxy-α-trifluoromethylphenyl-acetyl chloride (Mosher's reagent); ref. 12b.
29. (b) Dale, J. A.; Mosher, H. S. J. Am. Chem. Soc. 1973, 95, 512.
30. (a) Johnstone, R. A. W.; Wilby, A. H.; Entwistle, I. D. Chem. Rev. 1985, 85, 129.
31. (b) Bajwa, H. S. Tetrahedron Lett. 1992, 33, 2299.
32. Borch, R. F.; Hassid, A. I. J. Org. Chem. 1972, 37, 1673.
33. Sommerfeld, P.; Hoppe, D. Synlett 1992, 764.
34. Helmke, H.; Hoppe, D. Synlett 1995, 978.
35. (a) Eugster, C. H. Fortschr. Chem Org. Naturst. 1969, 27, 262.
36. (b) Matzinger, P.; Catalfomo, Ph.; Eugster, C. H. Helv. Chim. Acta 1972, 55, 1478.
37. γ-Hydroxy-norvalines are highly biologically active molecules, they increase insulin secretion, see: Ribes, G.; Broca, C.; Petit, P.; Jacob, M.; Baissac, Y.; Manteghatti, M.; Roye, M.; Sauvaire, Y. Diabetologia 1996, 39, A234.
38. (a) Schmeck, C.; Hegedus, L. S. J. Am. Chem. Soc. 1994, 116, 9927 and references cited therein.
39. (b) Harding, K. E.; Marman, T. H.; Nam, D.-h Tetrahedron Lett. 1988, 29, 1627.
40. (c) For preparation of racemate 32, see: Fischer, E.; Leuchs, L. Ber. Deutsch. Chem. Ces. 1902, 35, 3797.
41. Jacob, M.; Roumestant, M. L.; Viallefont, P.; Martinez, J. Synlett 1997, 691.
42. Nakajima, K.; Takai, F.; Tanaka, T.; Okawa, K. Bull. Chem. Soc. Jpn. 1978, 51, 1577.
43. Tomioka, H.; Takai, K.; Oshima, K.; Nozaki, H. Tetrahedron Lett. 1981, 22, 1605.
44. For the preparation of (2S,4S)-γ-hydroxy-norvaline (32) from the lactone hydrochloride 31 with i. 2 N NaOH, ii. Dowex 50WX8 (100%), see ref. 19.