An improved aqueous NBS–THF system in a range of media has proved to be effective for stereoselective construction of the bromotetrahydrofuran moiety of dihydroagarofuran sesquiterpene polyesters from the corresponding β-hydroxyalkene.
References
1.
(a) CrombieL., CrombieW. M. L., and WhitingD. A., The Alkaloids, ed. ManskeR. H. F., Academic Press, New York, 1990, vol. 39, pp. 139–164; (b) R. Brüning and H. Wagner, Phytochemistry, 1978, 17, 1821.
2.
KuoY.-H., KingM.-L., ChenC.-F., ChenH.-Y, ChenC.-H., ChenK., and LeeK.-H., J. Nat. Prod., 1994, 57, 263.
3.
TakaishiY., UjitaK., TokudaH., NishinoH., IwashimaA., and FujitaT., Cancer Lett., 1992, 65, 19.
4.
GonzalezA. G., JimenezI. A., RaveloA. G., and BazzocchiI. L., Tetrahedron, 1993, 49, 6637.
5.
HuffmanJ. W., DesaiR. C., and HillenbrandG. F., J. Org. Chem., 1984, 49, 982.
6.
WhiteJ. D., ShinH., KimT.-S., and CutshallN. S., J. Am. Chem. Soc.1997, 119, 2404.
7.
TuY. Q., and SunL. D., Tetrahedron Lett., 1998, 39, 7935.
8.
BillupsW. E., HaleyM. M., and LeeG.-A., Chem. Rev., 1989, 89, 1147.
9.
FredericksonM., and GriggR., Org. Prep. Proc. Int., 1997, 29, 35.
10.
CardilloG., and OrenaM., Tetrahedron, 1990, 46, 3321.
11.
KnappS., KukkolaP. J., SharmaS., DharT. G. M., and NaughtonA. B. J., J. Org. Chem., 1990, 55, 5700.