e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521
Iodocyclization of allylic alcohol derivatives containing internal nucleophiles. Control of stereoselectivity by substituents in the acyclic precursors
AR Chamberlin, M Dezube, P Dussault…
Index: Chamberlin; Dezube; Dussault; McMills Journal of the American Chemical Society, 1983 , vol. 105, # 18 p. 5819 - 5825
Abstract: The effect of various substituents on the diastereoselectivity of a number of kinetically controlled iodocyclizations has kn studied. The reaction of 3-hydroxy-4-alkenoic acids (la-n) with iodine in a neutral two-phase medium gives stereoselective ring closure, usually to the cis-3-hydroxy-4-iodoalkyl lactone. The stereoselectivity is unaffected by protection of alcohol moiety (lb, c), but replacement of the hydroxyl group with a methyl ...
