Radical-based asymmetric synthesis: An iterative approach to 1, 3, 5, ... (2n+1) polyols

[GRAPHICS] A conceptually novel approach to 1, 3, 5,... (2n + 1) polyols based on iter ative stereocontrolled homologation of chiral hydroxyalkyl radicals is repo rted. Starting from cx keto ester precursors, the general sequence of (1) k etone reduction, (2) auxiliary attachment, (3) saponification, (4) Barton e sterification, and (5) radical addition provided the two-carbon homologue i n 70-80% overall yield, The simplicity and generality of this iterative str ategy for 1, 3, 5,... (2n + 1) polyol synthesis suggests an attractive alte rnative for the preparation of molecules containing this structural motif.