P-Tether-Mediated, Iterative S_N2′-Cuprate Alkylation Strategy to Skipped Polyol Stereotetrads: Utility of an Oxidative “Function Switch” with Phosphite–Borane Tethers

Abstract

The development of a P-tether-mediated, iterative SN2’-cuprate alkylation protocol for the formation of 1,3-skipped polyol stereotetrads is reported. This two-directional synthetic strategy builds molecular complexity from simple, readily prepared C2-symmetric dienediols and unites the chemistry of both temporary phosphite-borane tethers and temporary phosphate tethers—through an oxidative “function switch” of the P-tether itself—to generate intermediates that were previously inaccessible via either method alone.

An Iterative Phosphate Tether Mediated Approach for the Synthesis of Complex Polyol Subunits

“…Interest in the development of methods to complex polyol formation and bioactive natural products and analogs , led to the titled study. Toward this goal, an iterative pot-efficient process for the synthesis of complex polyols is reported.…”