High-yield synthesis of a chiroporphyrin by hydrogen bond-directed cyclisation

Abstract

A new chiroporphyrin is prepared in 60% yield using complementary intramolecular hydrogen-bonding interactions between N-acylurea substituents to direct the cyclisation of the tetrapyrrolic intermediate; similar hydrogen-bond assistance by carboxylic acid functions is suggested for cyclisation of hydroxymethylbilane to uroporphyrinogen I.

References

1. M. Veyrat, L. Fantin, S. Desmoulins, A. Petitjean, M. Mazzanti, R. Ramasseul, J.-C. Marchon and R. Bau, Bull. Soc. Chim. Fr., 1997, 134, 703.
2. C. Pérollier, J. Pécaut, R. Ramasseul and J.-C. Marchon, Bull. Soc. Chim. Fr., 1997, 134, 517.
3. M. Veyrat, O. Maury, F. Faverjon, D. E. Over, R. Ramasseul, J.-C. Marchon, I. Turowska-Tyrk and W. R. Scheidt, Angew. Chem., Int. Ed. Engl., 1994, 33, 220; C. Pérollier, J. Pécaut, R. Ramasseul and J.-C. Marchon, Inorg. Chem., 1999, in the press..
4. J.-P. Simonato, J. Pécaut, W. R. Scheidt and J.-C. Marchon, Chem. Commun., 1999, 989.
5. M. Mazzanti, M. Veyrat, R. Ramasseul, J.-C. Marchon, I. Turowska-Tyrk, M. Shang and W. R. Scheidt, Inorg. Chem., 1996, 35, 3733.
6. D. Toronto, F. Sarrazin, J. Pécaut, J.-C. Marchon, M. Shang and W. R. Scheidt, Inorg. Chem., 1998, 37, 526.
7. J.-P. Simonato, J. Pécaut and J.-C. Marchon, J. Am. Chem. Soc., 1998, 120, 7363.
8. J. S. Lindsey and R. W. Wagner, J. Org. Chem., 1989, 54, 828.
9. C. Pérollier, Doctoral Thesis, Université Joseph Fourier, Grenoble, 1998.
10. For structurally characterised examples of strong dimerisation via complementary hydrogen bonding between urea N–H donors and amide C=O acceptors, see: F. H. Beijer, R. P. Sijbesma, H. Kooijman, A. L. Spek and E. W. Meijer, J. Am. Chem. Soc., 1998, 120, 6761.
11. For reviews of hydrogen-bonded self-assembling complexes, see: D. S. Lawrence, T. Jiang and M. Levitt, Chem. Rev., 1995, 95, 2229; M. M. Conn and J. Rebek, Jr., Chem. Rev., 1997, 97, 1467 For a previous example of macrocyclisation directed by hydrogen bonding, see: F. J. Carver, C. A. Hunter and R. J. Shannon, J. Chem. Soc., Chem. Commun., 1994, 1277.
12. For a recent review of heme biosynthesis, see: A. R. Battersby and F. J. Leeper, Top. Curr. Chem., 1998, 195, 143 For structurally characterised uroporphyrinogen derivatives, see: G. Sawitzki and H. G. von Schnering, Angew. Chem., Int. Ed. Engl., 1976, 15, 552; C. Lehmann, B. Schweizer, C. Leumann and A. Eschenmoser, Helv. Chim. Acta, 1997, 80, 1421.
13. S. Avramovici-Grisaru and S. Sarel, Nouv. J. Chim., 1982, 6, 455.