A Biomimetic Synthesis of a Porphobilinogen Precursor Using a Mukaiyama Aldol Reaction

Angewandte Chemie - International Edition

Volumn 37, Issue 3, 1998, Pages 358-360

  Chaperon, André R ^a   Engeloch, Thomas M ^a   Neier, Reinhard ^a  

^a UNIVERSITY OF NEUCHÂTEL   (Switzerland)

Author keywords

Aldol reactions; Biomimetic synthesis; Bioorganic chemistry; Porphobilinogen; Porphyrinoids

Indexed keywords

EID: 0032536557     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19980216)37:3<358::AID-ANIE358>3.0.CO;2-Y     Document Type: Article

References (36)

1. B. Franck, A. Nonn, Angew. Chem. 1995, 107, 1941-1957; Angew. Chem. Int. Ed. Engl. 1995, 34, 1795-1811.
2. B. Franck, A. Nonn, Angew. Chem. 1995, 107, 1941-1957; Angew. Chem. Int. Ed. Engl. 1995, 34, 1795-1811.
3. a) R. Neier in Advances in Nitrogen Heterocycles, Vol. 2 (Ed.: C. J. Moody). JAI Press, Greenwich, 1996, pp. 35-146;
4. b) P. M. Jordan in Biosynthesis of Tetrapyrroles (Ed.: P.M. Jordan), Elsevier, Amsterdam, 1991, pp. 1-66;
5. F. J. Leeper in Chlorophylls (Ed.: H. Scheer), CRC Press, Boca Raton, 1991, pp. 407-464;
6. A. R. Battersby, F. J. Leeper, Chem. Rev. 1990, 90, 1261-1274.
7. a) D. Mauzerall, J. Am. Chem. Soc. 1960, 82, 2605-2609;
8. b) ibid. 1960, 82, 2601-2605;
9. L. F. Tietze, H. Geissler, Angew. Chem. 1993, 105, 1087-1090; Angew. Chem. Int. Ed. Engl. 1993, 32, 1038-1040.
10. L. F. Tietze, H. Geissler, Angew. Chem. 1993, 105, 1087-1090; Angew. Chem. Int. Ed. Engl. 1993, 32, 1038-1040.
11. a) E. K. Jaffe, J. S. Rajagopalan, Bioorg. Chem. 1990, 18, 381-394;
12. b) B. Franck, H. Stratman, Heterocycles 1981, 75, 919-923;
13. A. I. Scott, C. A. Townsend, K. Okada, M. Kajiwara, Trans. N. Y. Acad. Sci. 1973, 55, 72-79.
14. a) D. Shemin in The Enzymes (Ed.: P. D. Boyer), Academic Press, New York, 1972, pp. 323-337;
15. b) D. L. Nandi, D. Shemin, J. Biol. Chem. 1968, 243, 1236-1242.
16. a) H. Bertschy, A. Meunier, R. Neier, Angew. Chem. 1990, 702, 828-830; Angew. Chem. Int. Ed. Engl. 1990, 29, 777-778;
17. a) H. Bertschy, A. Meunier, R. Neier, Angew. Chem. 1990, 702, 828-830; Angew. Chem. Int. Ed. Engl. 1990, 29, 777-778;
18. b) A. Meunier, R. Neier, Synthesis 1988, 381-383;
19. H. Bertschy, Dissertation, Universität Freiburg im Uechtland, 1991;
20. A. Meunier, Dissertation, Universität Freiburg im Uechtland, 1989.
21. a) T. Mukaiyama, Org. React. 1982, 28, 203-331;
22. b) Angew. Chem. 1977, 59, 858-866;
23. Angew. Chem. Int. Ed. Engl. 1977, 16, 817-825;
24. K. Banno, T. Mukaiyama, Chem. Lett. 1975, 741.
25. R. B. Frydman, B. Frydman, A. Valasinas in The Porphyrins, Vol. VI (Ed.: D. Dolphin), Academic Press, New York, 1979, pp. 1-123.
26. a) C. Y. De Leon, B. Ganem, Tetrahedron 1997, 53, 7731-7752;
27. b) J. Org. Chem. 1996, 67, 8730-8731;
28. M. Adamczyk, R. E. Reddy, Tetrahedron 1996, 52, 14689-14700;
29. Tetrahedron Lett. 1995, 36, 9121-9124.
30. R. D. Miller, D. R. McKean, Synthesis 1979, 730-732.
31. a) S. Murata, R. Suzuki, R. Noyori, J. Am. Chem. Soc. 1980, 702, 3248;
32. b) C. Mukai, S. Hashizume, K. Nagami, M. Hanaoka, Chem. Pharm. Bull. 1990, 38, 1509-1512.
33. A. P. Davis, M. Jaspars. Angew. Chem. 1992, 704, 475-477; Angew. Chem. Int. Ed. Engl. 1992, 57, 470-471.
34. A. P. Davis, M. Jaspars. Angew. Chem. 1992, 704, 475-477; Angew. Chem. Int. Ed. Engl. 1992, 57, 470-471.
35. 1).
36. G. W. Kenner, J. Rimmer, K. M. Smith, J. F. Unsworth, J. Chem. Soc. Perkin Trans, 1 1977, 332-340.