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

Org Lett. 2014 Nov 7;16(21):5824-6. doi: 10.1021/ol502956j. Epub 2014 Oct 27.

Abstract

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amides / chemical synthesis*
  • Amides / chemistry
  • Amino Alcohols / chemical synthesis*
  • Amino Alcohols / chemistry*
  • Catalysis
  • Isoxazoles / chemistry*
  • Molecular Structure
  • Oxazines / chemistry*
  • Ruthenium / chemistry*
  • Stereoisomerism

Substances

  • Amides
  • Amino Alcohols
  • Isoxazoles
  • N-(3-hydroxy-1-hydroxymethyl-3-phenylpropyl)dodecanamide
  • Oxazines
  • Ruthenium