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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

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journal contribution
posted on 07.11.2014 by Chuan-Zhi Yao, Zu-Feng Xiao, Xiao-Shan Ning, Jie Liu, Xiao-Wei Zhang, Yan-Biao Kang
A highly efficient ruthenium-catalyzed stereospecific N-demethylative 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.