The synthesis of three new polysubstituted cycloheptenones by cleavage of the ether bridge of 8-oxabicyclo[3.2.1]octan-3-one derivatives is described, together with the application of this methodology in the construction of the guaianolide and pseudoguaianolide skeleton.
References
1.
BarbosaL. C. A., RubingerM. M. M., MannJ., and MansellH. L., Tetrahedron, 1996, 52, 11927.
2.
RubingerM. M. M., MannJ., and DrewM. G. B., Tetrahedron, 1995, 51, 11295.
3.
StoherI., and HoffmannH. M. R., Tetrahedron, 1992, 48, 6021.
4.
MarfatA., and HelquistP., Tetrahedron Lett., 1978, 44, 4217.
5.
MarfatA., BalS. A., and HelquistP., J. Org. Chem., 1982, 47, 5045.
6.
CummingsW. J. M., DrewG. B., MannJ., and MarksonA. J., Tetrahedron, 1988, 44, 5151.
7.
HeathcockC. H., GermrothT. C., and GrahamS. L., J. Org. Chem., 1979, 44, 4481.
8.
BarbosaL. C. A., and MannJ., J. Chem. Soc., Perkin Trans. 1, 1990, 177.
