Radical-Based Asymmetric Synthesis:  An Iterative Approach to 1, 3, 5, ... (2<i>n</i> + 1) Polyols Philip Garner James T. Anderson 10.1021/ol990188v.s001 https://acs.figshare.com/articles/journal_contribution/Radical-Based_Asymmetric_Synthesis_An_Iterative_Approach_to_1_3_5_2_i_n_i_1_Polyols/3759753 A conceptually novel approach to 1, 3, 5, ... (2<i>n</i><i> </i>+ 1) polyols based on iterative stereocontrolled homologation of chiral hydroxyalkyl radicals is reported. Starting from α-keto ester precursors, the general sequence of (1) ketone reduction, (2) auxiliary attachment, (3) saponification, (4) Barton esterification, and (5) radical addition provided the two-carbon homologue in 70−80% overall yield. The simplicity and generality of this iterative strategy for 1, 3, 5, ... (2<i>n</i><i> </i>+ 1) polyol synthesis suggests an attractive alternative for the preparation of molecules containing this structural motif. 1999-09-04 00:00:00 homologue molecule iterative stereocontrolled homologation sequence novel approach generality alternative Barton Asymmetric saponification attachment iterative strategy polyols ester Synthesi simplicity chiral hydroxyalkyl radicals Iterative Approach esterification keto Polyol precursor motif preparation ketone polyol synthesis