Unlike other acidic systems, the tetracyanoethylene catalysed methanolysis of androstane 2,3-epoxides proceeds normally without giving products arising from the transannular participation of a 5α,6α-epoxide, a 5α-hydroxy group or a 5(6)-ene.
References
1.
MasakiY., MiuraT. and OchiaiM., Synlett., 1993, 847.
2.
BoyntonJ. A., HansonJ. R. and UyanikC., J. Chem. Res. (S), 1995, 334.
3.
HansonJ. R., HitchcockP. H. and KiranI., J. Chem. Res., 1999, (S) 356; (M) 1581.
4.
HansonJ. R., HitchcockP. B. and UyanikC., J. Chem. Res., 1998, (S) 300; (M) 1366.
5.
ColladoI. G., HansonJ. R. and Macias-SanchezA. J., Tetrahedron, 1996, 52, 7961.
6.
KocovskyP. and CernyV., Coll. Czech. Chem. Commun., 1979, 44, 1496.