Synthesis of syn-1,3-Aminoalcohols via a Ru-Catalyzed N-Demethylative Rearrangement of Isoxazolidines and Its Application in a Three-Step Total Synthesis of HPA-12

摘要

A highly efficient ruthenium-catalyzed stereospecific Ndemethylative rearrangement of isoxazolidines to synthetically useful N?H-1,3-oxazinanes is described. 1,3-Oxazinanes are useful building blocks, which can be further converted to N?H-1,3-aminoalcohols in one step. This new method was used in a three-step gram-scale total synthesis of HPA-12 in an overall 24% yield.