A route has been developed for the enantioselective synthesis of (4R,5S)-O-acetylosmundalactone 1 and (4S,5R)-O-acetylosmundalactone 2 by using Sharpless kinetic resolution of the racemic 1-(2-furyl)ethanol 6 as a key step.
References
1.
NumataA., HokimotoK., and KatsunoT., Chem. Pharm. Bull., 1984, 32, 2815.
2.
BuchananM. S., and HashimotoT., Phytochemistry, 1995, 40, 1251.
3.
HollenbeakK. H., and KuechneM. E., Tetrahedron, 1974, 30, 2307.
4.
StevenV. L., and ArmstrongA., J. Chem. Soc., Perkin Trans. 1, 1991, 667.
5.
KusakabeM., KitanoY., and KobayashiY., J. Org. Chem., 1988, 53, 1586.
6.
(a) RosenbrookW., and CarneyR. E., Tetrahedron Lett., 1990, 31, 1867; (b) A. D. Argougelis and J. F. Zierserl, Tetrahedron Lett., 1966, 7, 1969; (c) R. H. Evans and G. A. Ellestad, Tetrahedron Lett., 1969, 10, 1791; (d) H. Achembach and G. Wittmann, Tetrahedron Lett., 1970, 21, 3259.