A correlation between the position of the 13C NMR signal for the C-10 methyl group (C-19) and the stereochemistry of the A/B ring junction has been established and applied to the determination of the stereochemistry of the products of the hydroboration of B-norandrosta-3,5-dien-17-one.
References
1.
AllingerN. L., and TribbleM. T., Tetrahedron, 1972, 28, 1191.
2.
KasalA., and JoskaJ., Collect. Czech. Chem. Commun., 1972, 37, 2234.
3.
DjerassiC., MarshallD., and NakanoT., J. Am. Chem. Soc., 1958, 80, 4856.
4.
BluntJ. W., and StothersJ. B., Org. Magn. Reson., 1977, 9, 439.
5.
BoyntonJ. A., HansonJ. R., and LimanM. D., J. Chem. Res., 1998, (S) 376; (M) 1616.
6.
SheldrickG. M., SHELXS-86 Program for the Solution of Crystal Structures, University of Gottingen, Germany, 1985.
7.
SheldrickG. M., SHELXL-93 Program for Crystal Structure Refinement, University of Gottingen, Germany, 1993.
