The highly diastereoselective addition of organometallic derivatives of trimethylsilylacetylen to N-Boc-O-Me-L-thyrosinal - Synthesis directed towards anisomycin

Arkivoc

Volumn 2004, Issue 3, 2004, Pages 112-119

  Gruza, Henryk ^a   Gryko, Dorota ^a   Jurczak, Janusz ^a,b  

^a INSTITUTE OF ORGANIC CHEMISTRY   (Poland)

^b UNIVERSITY OF WARSAW   (Poland)

Author keywords

Amino aldehydes; Acetylenic addition; Anisomycin; Asymmetric synthesis

Indexed keywords

ACETYLENE DERIVATIVE; ANISOMYCIN; N TERT BUTYLOXYCARBONYL O METHYLTHYROSINAL; ORGANOMETALLIC COMPOUND; TRIMETHYLSILYLACETYLENE; TYROSINE; TYROSINE DERIVATIVE; UNCLASSIFIED DRUG; ZINC BROMIDE;

ADDITION REACTION; AMINO ACID SYNTHESIS; ARTICLE; CHEMICAL STRUCTURE; DIASTEREOISOMER; DRUG SYNTHESIS; STEREOCHEMISTRY;

EID: 2942616972     PISSN: 14246376     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (39)

1. Sobin, B. A.; Tanner, F. W. J. Am. Chem. Soc. 1954, 76, 4053.
2. Korzybski, T.; Kowszyk-Gindifer, Z.; Kurylowicz, W. Antibiotics, Vol. 1, American Society of Microbiology, Washington DC, 1978, 343.
3. The Merck Index, 12th ed., Budavari, S., Ed., Merck: Whitehouse Station, NJ, 1996, 710.
4. Hosoya, Y.; Kameyama, T.; Naganawa, H.; Okami Y.; Takeuchi T. J. Antibiotics, 1993, 46, 1300.
5. Bereboom, J. J.; Butler, K.; Pennington, F. C.; Solomons, I. A. J. Org. Chem. 1965, 30, 2334.
6. Schaefer, J. P.; Weatley, P. J. J. Org. Chem. 1968, 33, 166.
7. Wong, C. M. Can. J. Chem. 1968, 46, 1101.
8. Merino, P.; Frnco, S.; Lafuente, D.; Merchan, F.; Revuelta, J.; Tejero, T. Eur. J. Org. Chem. 2003, 2877.
9. Chang, M-Y.; Chen, S-T.; Chang, N-C. Heterocycles 2003, 60, 1203.
10. Huang, P-Q.; Zheng, X. ARKIVOC: 2003, part 2, 7.
11. Chandrasekhar, S.; Ramachandar, T.; Venkat Reddy, M. Synthesis 2002, 1867.
12. Hulme, A. N.; Rosser, E. M. Org. Lett. 2002, 4, 265 and references cited herein.
13. Chang, K-T.; Chang Jang, K.; Park, H-Y.; Kim, Y-K.; Park, K. H.; Lee, W. S. Heterocycles 2001, 55, 1173. Huang, P. Q.; Tang, X.; Chen, A. Q. Synth. Commun. 2000, 30, 2259.
14. Chang, K-T.; Chang Jang, K.; Park, H-Y.; Kim, Y-K.; Park, K. H.; Lee, W. S. Heterocycles 2001, 55, 1173. Huang, P. Q.; Tang, X.; Chen, A. Q.Synth. Commun. 2000, 30, 2259.
15. Jäger, V.; Öhrlein, R.; Wehner, V.; Poggendorf, P.; Steuer, B. ; Raczko, J.; Greisser, H.; Keiss, F-M.; Menzel, A. Enantiomer 1999, 4, 205.
16. Ono, M.; Suzuki, K.; Akita, H. Tetrahedron Lett. 1999, 40, 8223.
17. Gryko, D.; Prokopowicz, P.; Jurczak, J. Tetrahedron: Asymmetry 2002, 13, 1103.
18. Jurczak, J.; Prokopowicz, P.; Gołȩbiowski, A. Tetrahedron Lett. 1993, 34, 7107.
19. Gryko, D.; Jurczak, J. Polish J. Chem. 2002, 76, 959.
20. Gryko, D.; Jurczak, J. Tetrahedron Lett. 1997, 38, 8275.
21. Krasiński, A.; Gruza, H.; Jurczak, J. Tetrahedron: Asymmetry 2001, 12, 111.
22. Krasiński, A.; Jurczak, J. Tetrahedron Lett. 2001, 42, 2019.
23. Gołȩbiowski, A.; Jurczak, J. Synlett 1993, 241.
24. Kiciak, K.; Jakobson, U.; Gołȩbiowski, A.; Jurczak, J. Polish J. Chem. 1994, 68, 199.
25. Jurczak, J. in Preparative Carbohydrate Chemistry; Hanessian, S. Ed.; Dekker: NJ, 1997, 593.
26. Gryko, D.; Chałko, J.; Jurczak, J. Chirality 2003, 15, 514.
27. Kobrzycka, E.; Gryko, D.; Jurczak. Tetrahedron: Asymmetry 2002, 13, 2133.
28. Gryko, D.; Jurczak, J. Helv. Chim. Acta 2000, 83, 2705.
29. Gruza, H.; Kiciak, K.; Krasiński, A.; Jurczak, J.Tetrahedron: Asymmetry 1997, 8, 2627.
30. Jurczak, J.; Gryko, D.; Kobrzycka, E.; Gruza, H.; Prokopowicz, P. Tetrahedron 1998, 54, 6051.
31. Cherest, M.; Felkin, H.; Prudent, N. Tetrahedron Lett. 1968, 18, 1245.
32. Anh, N. T. Topics Curr. Chem. 1980, 88, 114.
33. Cram, D. J.; Wilson, D. R. J. Am. Chem. Soc. 1982, 104, 5719.
34. Cai, C.; Vasella, A. Helv. Chim. Acta. 1995, 78, 732.
35. Organic Synthesis 1985,64, 108.
36. Höfle, I.; Steglich, W.; Vorbrüggen, H. Angew. Chem. Int. Ed.1978, 17, 569.
37. Jarosz, S. Polish J. Chem. 1992, 66, 1853.
38. Fürst, A.; Koller, F. Helv. Chim. Acta. 1947, 30, 1454.
39. Schwardt, O.; Veith, U.; Gaspard, Ch.; Jäger, V. Synthesis, 1999, 1473.