Combinatorial chemistry of natural products: Solid phase synthesis of D- and L-cycloserine derivatives

Tetrahedron

Volumn 54, Issue 52, 1998, Pages 15879-15890

  Gordeev, Mikhail F ^a   Luehr, Gary W ^a   Hui, Hon C ^a   Gordon, Eric M ^a   Patel, Dinesh V ^a  

^a Versicor Inc   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

9 FLUORENYLMETHYL CHLOROFORMATE; AMINE; CYCLOSERINE; NATURAL PRODUCT; PIPERIDINE DERIVATIVE; REAGENT; RESIN; SILANE DERIVATIVE; TRITYL DERIVATIVE;

ACYLATION; ARTICLE; DRUG DESIGN; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; NONHUMAN; PHYTOCHEMISTRY; PRIORITY JOURNAL; SOLID PHASE EXTRACTION;

EID: 0032564564     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00997-1     Document Type: Article

References (38)

1. 1. See, e.g., reviews: (a) Gordon, E. M.; Barrett, R. W.; Dower, W. J.; Fodor, S. P. A.; Gallop, M. A. J. Med. Chem. 1994, 37, 1385;
2. (b) Gordon, E. M. Current Opinion in Biotechnology. 1995, 6, 624;
3. (c) Gordon, E. M.; Gallop, M. A.; Patel, D. V. Acc. Chem. Res. 1996, 29; 144;
4. (d) Patel, D. V.; Gordon, E. M. Drug Discovery Today. 1996, 134;
5. (e) Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555;
6. (f) Hermkens, P. P. H.; Ottenheijm, H. C. J.; Rees, D. Tetrahedron. 1996, 52, 4527;
7. (g) Patel, D. V.; Gordon, E. M. Drug Discovery Today. 1996, 1, 134;
8. (g) Gordeev, M. F.; Patel, D. V. In: Combinatorial Chemistry and Molecular Diversity in Drug Discovery. Eds. E. M. Gordon and J. F. Kerwin. 1998, in press.
9. 2. For an early account, see: (a) Crowley, J. I.; Rapoport, H. Acc. Chem. Res. 1976, 9, 135. The topic has been recently reviewed in ref.
10. (b) Sofia, M. J. In: Combinatorial Chemistry and Molecular Diversity in Drug Discovery. Eds. E. M. Gordon and J. F. Kerwin. 1998, in press.
11. 3. Atuegbu, A.; Maclean, D.; Nguyen, C.; Gordon, E. M.; Jacobs, J. W. Bioorg. Med. Chem. 1996, 4, 1097.
12. 4. Nicolaou, K. C.; Winssinger, N.; Pastor, J.; Ninkovic, S.; Sarabia, F.; He, Y.; Vourloumis, D.; Yang, Z.; Li, T.; Giannakakou, P.; Hamel, E. Nature (London). 1997, 387, 268.
13. 5. Xiao, X.-Y.; Parandoosh, Z.; Nova, M. P. J. Org. Chem. 1997, 62, 6029.
14. 6. Chen, S.; Janda, K. D. W. J. Am. Chem. Soc. 1997, 119, 8724.
15. 7. De Amici, M.; De Micheli, C. D.; Cateni, F.; Carrea, G.; Ottolina, G. Tetrahedron: Asymmetry. 1993, 4, 1073.
16. 8. (a) Strominger, J. L.; Threnn, R. H.; Scott, S.S. J. Am. Chem. Soc. 1959, 81, 3803;
17. (b) Ito, E.; Stromiger, J. L. J. Biol. Chem. 1962, 237, 2696;
18. (c) Neuhaus, F. C.; Lynch, J. L. Biochemistry, 1964, 3, 471;
19. (d) Gale, I. F.; Cuncliffe, E.; Reynolds, P. E.; Richmond, M. H.; Waring, M. J. In: The Molecular Basis of Antibiotic Action. John Wiley & Sons, 1981, p.65.
20. 9. Nozaki, Y.; Katayama, N.; Ono, H.; Tsubotani, S.; Harada, S.; Okazaki, H.; Nakao, Y. Nature (London), 1987, 325, 179; Critical Rev. Biotech. 1992, 12, 225.
21. 9. Nozaki, Y.; Katayama, N.; Ono, H.; Tsubotani, S.; Harada, S.; Okazaki, H.; Nakao, Y. Nature (London), 1987, 325, 179; Critical Rev. Biotech. 1992, 12, 225.
22. 10. Nozaki, Y.; Katayama, N.; Harada, S.; Ono, H.; Okazaki, H. J. Antibiot. (Tokyo), 1989, 42, 84.
23. 11. SciFinder search in CAS data base (1965 - present) has produced ca. 171 and 4246 hits for topics "synthesis of cycloserines" and "synthesis of β-lactams", respectively.
24. 12. Herein, we employ the terms "a scaffold decoration" and "a total synthesis" to describe two different combichem strategies. In the former, the key scaffold building block is produced in solution, immobilized, and then derivatized on a solid phase. In the second approach, the scaffold itself is constructed via SPS starting from an appropriate immobilized precursor reagent.
25. 13. Payne, R. A.; Stammer, C. H. J. Org. Chem. 1968, 33, 2421. Notably, the authors also described a solution phase N-tritylation of the D-cycloserine ortho-salicylimine.
26. 14. Baldwin, J. E.; Ng, S. C.; Pratt, A. J. Tetrahedron Lett. 1987, 28, 4319.
27. 15. Attempts to employ several other amine protection groups, such as benzaldimine and ortho-salicylimine functionalities were less satisfactory.
28. 16. Polystyrene-based 2-methoxy-4-alkoxybenzyl alcohol resin: Mergler, M.; Tanner, R.; Gosteli, J.; Grogg, P. Terahedron Lett. 1988, 29, 4005.
29. 17. Barlos, K, et al. Tetrahedron Lett. 1989, 30, 3947.
30. 20 have been well documented, no Mitsunobu-type transformation of cycloserine derivatives has been reported.
31. 19. (a) Payne, R. A.; Stammer, C. H. J. Org. Chem. 1968, 33, 2421;
32. (b) Baldwin, J. E.; Ng, S. C.; Pratt, A. J. Tetrahedron Lett. 1987, 28, 4319.
33. 20. See, e.g. a review: Mitsunobu, O. Synthesis 1981, 1.
34. 21. Carpino, L. A.; Han, G. Y. J. Org. Chem. 1972, 37, 3404.
35. 16 with that for acidolytically more stable PAL amide analogs derived from 2,6-dimethoxy-4-alkoxybenzylamine resin: Albericio, F.; Barany, G. Int. Pept. Protein Res. 1987, 30, 206.
36. 23. A preference for certain types of polymeric supports in specific chemical transformations is well documented: see, e.g. (a) Gordeev, M. F.; Patel, D. V.; Gordon, E. M. J. Org. Chem. 1997, 62, 8177;
37. (b) Czarnik, A. Biotech. Bioeng. (Combin. Chem.). 1998, 61, 77.
38. 2O resonances (AB part of the ABX cycloserine system), whereas a single multiplet for the α-proton of D-Ala fragment observed (δ 5.57 ppm). Interestingly, little or no racemization has been detected in a similar base-mediated heterocyclization with a dipeptidic analog of the urea 22: Gordeev, M. F.; Hui. H. C.; Gordon, E. M.; Patel, D. V. Tetrahedron Lett. 1997, 38, 1729. Absolute configuration for the two diastereomers 23 was not determined.