Some Rearrangements of Gibberellins Catalysed by Tetracyanoethylene

Abstract

Tetracyanoethylene in methanol has been shown to catalyse the rearrangement of ring A of gibberellic acid to the3β-methyl ether of gibberellenic acid and to the 19-2α-isolactone whilst the 13-hydroxygibberellin 16,17-epoxides are converted to 8:13-isogibberellins.

References

1. Y. Masaki, T. Miura and M. Ochiai, Synlett, 1993, 847.
2. Y. Masaki, T. Miura and M. Ochiai, Bull. Chem. Soc. Jpn., 1996, 69, 195.
3. J. A. Boynton, J. R. Hanson and C. Uyanik, J. Chem. Res. (S), 1995, 334.
4. J. R. Hanson, P. B. Hitchcock and C. Uyanik, J. Chem. Res., 1998, (S) 300, (M) 1366.
5. I. G. Collado, J. R. Hanson and A. J. Macias-Sanchez, Tetrahedron, 1996, 52, 7961.
6. I. G. Collado, J. R. Hanson, R. Hernandez-Galan, P. B. Hitchcock, A. J. Macias-Sanchez and J. C. Racero, Tetrahedron, 1998, 54, 1615.
7. For a review see J. R. Hanson, Nat. Prod. Rep., 1990, 7, 41.
8. B. E. Cross, J. Chem. Soc., 1954, 4670.
9. K. Schreiber, G. Schneider and G. Sembdner, Tetrahedron, 1968, 24, 73.
10. A. G. Avent, M. K. Baynham, J. R. Hanson, P. B. Hitchcock and B. H. de Oliveira, J. Chem. Soc., Perkin Trans. 1, 1989, 627.
11. T. Sato, J. Otera and H. Nozaki, J. Org. Chem., 1992, 57, 2166.