Ueno-Stork Cyclization

Y. Ueno et al., J. Am. Chem. Soc. 104, 5564 (1982); G. Stork et al., ibid. 105, 3741 (1983).

Radical cyclization of haloacetals. The cyclic acetal product can be converted to a lactone via Jones Oxidation, q.v.:

Synthetic applications: Y. Ueno et al., J. Chem. Soc. Perkin Trans. 1 1986, 1351; G. Stork et al., J. Am. Chem. Soc. 108, 6384 (1986); F. Villar et al., Org. Lett. 2, 1061 (2000); G. K. Friestad, G. M. Fioroni, ibid. 7, 2393 (2005). Stereochemistry studies: F. Villar et al., Chem. Eur. J. 9, 1566 (2003); O. Corminboeuf et al., ibid. 1578. Review: X. J. Salom-Roig et al., Synthesis 2004, 1903-1928.