Synthesis of (2S,3R,4S)-isonorstatine using a solvent-induced highly stereoselective 3-butenyl addition to L-threose imines

Synthesis

Volumn , Issue 13, 2006, Pages 2173-2182

  Li, Feng ^a   Schwardt, Oliver ^a   Jäger, Volker ^a  

^a UNIVERSITY OF STUTTGART   (Germany)

Author keywords

Allyl 1 butene 3 yl addition; Aminohydroxymethyl acid; N (1 phenylethyl) auxiliary; Solvent effect; Threose imines

Indexed keywords

ADDITION REACTIONS; CARBOXYLIC ACIDS; SOLVENTS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL); XYLOSE;

ALLYL/1-BUTENE-3-YL ADDITION; AMINOHYDROXYMETHYL ACID; N-(1-PHENYLETHYL) AUXILIARY; SOLVENT EFFECT; THREOSE IMINES;

BUTENES;

1 BUTEN 3 YL; 2 O BENZYL 3,4 O ISOPROPYLIDENE 1 THREOSE N (1' PHENYLETHYL)IMINE; 3 AMINO 2 BENZYLOXY 4 METHYL N (1' PHENYLETHYL)HEXANOIC ACID; 3 AMINO 4 O BENZYL 4,6 DIHYDROXY 3 N (1' PHENYLETHYL) 5 HEXANOLIDE; 3 AMINO 4 O BENZYL 5,6 O ISOPROPYLIDENE 2 METHYL 3 N (1' PHENYLETHYL)HEXANOIC ACID; 3 AMINO 4,6 DIHYDROXY 3 N (1' PHENYLETHYL) 5 HEXANOLIDE; 3 BUTENYL; 4 AMINO 2 O BENZYL 1,2 O ISOPROPYLIDENE 5 METHYL 4 N (1' PHENYLETHYL)HEPTANE 1,2,3,67 PENTOL; 4 AMINO 3 O 4 N DIBENZYL 1,2 O ISOPROPYLIDENE 5 METHYL 1,2,3 HEPTANETRIOL; 4 AMINO 3 O BENZYL 1,2 O ISOPROPYLIDENE 5 METHYL N (1' PHENYLETHYL) 6 HEPTENE 1,2,3 TRIOL; 4 AMINO 3 O BENZYL 1,2 O ISOPROPYLIDENE 6 METHYL N (1' PHENYLETHYL) 6 HEPTENE 1,2,3 TRIOL; 4 AMINO 3 O BENZYL 5 METHYL N (1' PHENYLETHYL) 1,2,3 HEPTANETRIOL; 4 AMINO 3 O BENZYL 5 METHYL N (1' PHENYLETHYL) 6 HEPTENE 1,2,3 TRIOL; 4 AMINO 3 O, 4 N DIBENZYL 1,2 O ISOPROPYLIDENE 6 HEPTENE 1,2,3 TRIOL; BUTANE; DIMETHYL 2 O BENZYL 4 METHYL 3 N (1' PHENYLETHYL)PENTANEDIOATE; GAMMA BENZYLOXY DELTA LACTONE; GAMMA HYDROXY DELTA LACTONE; HYDROXYAMINO ACID; IMINE; ISONORSTATINE; KETONE DERIVATIVE; LACTONE; METHYL 3 AMINO 4 O BENZYL 5,6 O ISOPROPYLIDENE 2 METHYL 3 N (1' PHENYLETHYL)HEXANOATE; N (1 PHENYLETHYL)IMINE; STATINE DERIVATIVE; TARTARIC ACID; THREOSE; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

ADDITION REACTION; ARTICLE; DRUG CONFORMATION; DRUG STRUCTURE; DRUG SYNTHESIS; SOLVENT EFFECT; STEREOCHEMISTRY;

EID: 33746082033     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-942426     Document Type: Article

References (69)

1. β-Amino acids: (a) Schmidt, U.; Kroner, M.; Griesser, H. Synthesis 1989, 832.
2. (b) Juaristi, E.; Quintana, D.; Lamatsch, B.; Seebach, D. J. Org. Chem. 1991, 56, 2553.
3. (c) Enantioselective Synthesis of β-Amino Acids; Juaristi, E., Ed.; Wiley-VCH: New York, 1977.
4. (d) Hill, D. J.; Mio, M. J.; Prince, R. B.; Hughes, T. S.; Moore, J. S. Chem. Rev. 2001, 101, 3893.
5. (e) Cheng, R. P.; Gellman, S. H.; DeGrado, W. F. Chem. Rev. 2001, 101, 3219.
6. (f) Minter, A. R.; Fuller, A. A.; Mapp, A. K. J. Am. Chem. Soc. 2003, 125, 6846.
7. (g) Zhao, Y. H.; Jiang, N.; Chen, S. F.; Peng, C.; Zhang, X. M.; Zou, Y. P.; Zhang, S. W.; Wang, J. W. Tetrahedron 2005, 61, 6546.
8. β-Amino hydroxy acids: (a) Rich, D. H. In Comprehensive Medicinal Chemistry, Vol. 1; Hansh, C.; Sammes, P. G.; Taylor, J. B., Eds.; Pergamon: Oxford, 1990.
9. (b) Huff, J. R. J. Med. Chem. 1991, 34, 2305.
10. (c) Thaisrivongs, S. Annu. Rep. Med. Chem. 1994, 133.
11. (d) Umezawa, H.; Aoyagi, T.; Morishima, H.; Matzusaki, M.; Hamada, H.; Tabeuchi, T. J. Antibiot. 1970, 23, 259.
12. (a) Rich, D. H.; Moon, B. J.; Boparai, A. S. J. Org. Chem. 1980, 45, 2288.
13. (b) Rich, D. H.; Moon, B. J.; Harbeson, S. J. Med. Chem. 1984, 27, 417.
14. (c) Sugimura, H.; Miura, M.; Yamada, N. Tetrahedron: Asymmetry 1997, 8, 4089.
15. (a) Iizuka, K.; Kamijo, T.; Kubota, T.; Akahane, K.; Umeyama, H.; Kiso, Y. J. Med. Chem. 1988, 31, 704.
16. (b) Iizuka, K.; Kamijo, T.; Harada, H.; Akahane, K.; Kubota, T.; Umeyama, H.; Kiso, Y. J. Chem. Soc., Chem. Commun. 1989, 1678.
17. Iizuka, K.; Kamijo, T.; Harada, H.; Akahane, K.; Kubota, T.; Etoh, Y.; Shimaoka, I.; Tsubaki, A.; Murakami, M.; Yamaguchi, T.; Iyobe, A.; Umeyama, H.; Kiso, Y. Chem. Pharm. Bull. 1990, 38, 2487.
18. Iizuka, K.; Kamijo, T.; Harada, H.; Akahane, K.; Kubota, T.; Umeyama Ishida, T.; Kiso, Y. J. Med. Chem. 1990, 33, 2707.
19. (a) Jäger, V. ; Wehner, V. Angew. Chem., Int. Ed. Engl. 1989, 28, 469.
20. (b) Kieß, F.-M.; Poggendorf, P.; Picasso, S.; Jäger, V. Chem. Commun. 1998, 119.
21. (c) Menzel, A.; Öhrlein, R.; Griesser, H.; Jäger, V. Synthesis 1999, 1691.
22. (d) Review: Jäger, V.; Öhrlein, R.; Wehner, V.; Poggendorf, P.; Steuer, B.; Raczko, J.; Griesser, H.; Kieß, F.-M.; Menzel, A. Enantiomer 1999, 4, 205; and references cited therein.
23. Reviews: (a) Risch, N.; Arend, M. In Houben-Weyl, Methoden der Organischen Chemie, 4th ed., Vol. E21b; Helmchen, G.; Hoffmann, R. W.; Mulzer, J.; Schaumann, E., Eds.; Thieme: Stuttgart, 1995, 1833.
24. (b) Enders, D.; Reinhold, U. Tetrahedron: Asymmetry 1997, 8, 1895.
25. (c) Bloch, R. Chem. Rev. 1998, 98, 1047.
26. For related additions to ribose imines see: (d) Lay, L.; Nicotra, F.; Paganini, A.; Pangrazio, L.; Panza, L. Tetrahedron Lett. 1993, 34, 4555.
27. (e) Cippola, L.; Lay, L.; Nicotra, F.; Pangrazio, L.; Panza, L. Tetrahedron 1995, 51, 4679.
28. (f) Kleemann, H.-W.; Heitsch, H.; Henning, R.; Kramer, W.; Kocher, W.; Lerch, U.; Linz, W.; Nickel, W.-U.; Ruppert, D.; Urbach, H.; Utz, R.; Wagner, A.; Week, R.; Wiegand, F. J. Med. Chem. 1992, 35, 59.
29. (g) Clark, R. D.; Jahangir; Souchet, M.; Kern, J. R. J. Chem. Soc., Chem. Commun. 1989, 930.
30. (a) Franz, T.; Hein, M.; Veith, U.; Jäger, V.; Peters, E.-M.; Peters, K.; von Schnering, H. G. Angew. Chem., Int. Ed. Engl. 1994, 33, 1298.
31. (b) Veith, U.; Leurs, S.; Jäger, V. J. Chem. Soc., Chem. Commun. 1996, 329.
32. (a) Veith, U.; Schwardt, O.; Jäger, V. Synlett 1996, 1181.
33. (b) Schwardt, O.; Veith, U.; Gaspard, C.; Jäger, V. Synthesis 1999, 1473.
34. Meunier, N.; Veith, U.; Jäger, V. J. Chem. Soc., Chem. Commun. 1996, 331.
35. (a) Steuer, B.; Wehner, V.; Lieberknecht, A.; Jäger, V. Org. Synth. 1996, 74, 1.
36. (b) Steuer, B. Dissertation; Universität Stuttgart: Germany, 1995.
37. (a) Veith, U. Dissertation; Universität Stuttgart: Germany, 1995.
38. (b) Schwardt, O. Dissertation; Universität Stuttgart: Germany, 1999.
39. (a) Fujita, K.; Nakai, H.; Kobayashi, S.; Inoue, K.; Nojima, S.; Ohno, M. Tetrahedron Lett. 1982, 23, 3057.
40. (b) Al-Hakim, A. H.; Haines, A. H.; Morley, C. Synthesis 1985, 207.
41. (c) Valverde, S.; Herradón, B.; Martin-Lomas, M. Tetrahedron Lett. 1985, 26, 3731.
42. (d) Sánchez-Sancho, F.; Valverde, S.; Herradón, B. Tetrahedron: Asymmetry 1996, 7, 3029.
43. (e) Collins, J. C.; Hess, W. W.; Frank, F. J. Tetrahedron Lett. 1968, 3363.
44. (f) Ratcliffe, R. W. Org. Synth. 1976, 55, 84.
45. (g) Texier-Boullet, F. Synthesis 1985, 679.
46. Krämer, B.; Franz, T.; Picasso, S.; Pruschek, P.; Jäger, V. Synlett 1997, 295.
47. For related allyl additions to both α- and β-alkoxyimines, see: (a) Yamamoto, Y.; Komatsu, T.; Maruyama, K. J. Am. Chem. Soc. 1984, 106, 5031.
48. (b) Yamamoto, Y.; Komatsu, T.; Maruyama, K. J. Org. Chem. 1985, 50, 3115.
49. (c) Yamamoto, Y.; Komatsu, T.; Maruyama, K. J. Chem. Soc., Chem. Commun. 1985, 814.
50. (d) Yamamoto, Y.; Ito, W.; Maruyama, K. J. Chem. Soc., Chem. Commun. 1985, 1131.
51. (e) Yamamoto, Y.; Nishii, S.; Maruyama, K.; Komatsu, T.; Ito, W. J. Am. Chem. Soc. 1986, 108, 7778.
52. (f) Yamamoto, Y.; Ito, W. Tetrahedron 1988, 44, 5415.
53. (g) Nakamura, H.; Iwama, H.; Yamamoto, Y. Chem. Commun. 1996, 1459.
54. (h) Nakamura, H.; Iwama, H.; Yamamoto, Y. J. Am. Chem. Soc. 1996, 118, 6641.
55. (i) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207.
56. (j) Hoppe, D. In Houben-Weyl, Methoden der Organischen Chemie, 4th ed., Vol. E21b; Helmchen, G.; Hoffmann, R. W.; Mulzer, J.; Schaumann, E., Eds.; Thieme: Stuttgart, 1995, 1401.
57. A related strategy has been applied to the synthesis of both enantiomers of goniofufurone from D-glucose where the termini were selectively transformed into allyl alcohol moieties suitable for ensuing oxycarbonylation:
58. (a) Gracza, T.; Jäger, V. Synlett 1992, 191.
59. (b) Gracza, T.; Jäger, V. Synthesis 1994, 1359.
60. (c) Jäger, V.; Gracza, T.; Dubois, E.; Hasenöhrl, T.; Hümmer, W.; Kautz, U.; Kirschbaum, B.; Lieberknecht, A.; Remen, L.; Shaw, D.; Stahl, U.; Stephan, O. Proceedings of the Fifth Symposium OSM5 in Organic Synthesis via Organometallics; Helmchen, G., Ed.; Vieweg: Braunschweig/ Wiesbaden, 1997, 331.
61. (a) Kraus, G. A.; Roth, B. J. Org. Chem. 1980, 45, 4825.
62. (b) Lindgren, B. O.; Hilsson, T. Acta Chem. Scand. 1973, 27, 888.
63. For related uses of acetal-protected diols as a latent carboxyl group see, for example, synthesis of furanomycin and its analogues: (a) Zimmermann, P. J.; Blanarikova, I.; Jäger, V. Angew. Chem. Int. Ed. 2000, 39, 910.
64. (b) Lee, J. Y.; Schiffer, G.; Jäger, V. Org. Lett. 2005, 7, 2317.
65. (c) Zimmermann, P. J.; Lee, J. Y.; Hlobilova, I.; Endermann, R.; Häbich, D.; Jäger, V. Eur. J. Org. Chem. 2005, 3450.
66. (d) Henneböhle, M.; Le Roy, P.-Y.; Hein, M.; Ehrler, R.; Jäger, V. Z. Naturforsch., B 2004, 59, 451; and references therein.
67. (e) Portolés, R.; Murga, J.; Falomir, E.; Carda, M.; Uriel, S.; Marco, J. A. Synlett 2002, 711.
68. Sharpless, K. B.; Amberg, W.; Bennani, Y. L.; Crispino, G. A.; Hartung, J.; Jeong, K.-S.; Kwong, H.-L.; Morikawa, K.; Wang, Z.-M.; Xu, D.; Zhang, X.-L. J. Org. Chem. 1992, 57, 2768.
69. Sun, X. C.; Rodriguez, M.; Zeckner, D.; Sachs, B.; Current, W.; Boyer, R.; Paschal, J.; McMillian, C.; Chen, S. H. J. Med. Chem. 2001, 44, 2671.