title: 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.
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.
authors.affiliation: Department of Chemistry, University of Science and Technology of China , Hefei, Anhui 230026, China.
authors.forename: Chuan-Zhi
authors.initials: CZ
authors.lastname: Yao
authors.forename: Zu-Feng
authors.initials: ZF
authors.lastname: Xiao
authors.forename: Xiao-Shan
authors.initials: XS
authors.lastname: Ning
authors.forename: Jie
authors.initials: J
authors.lastname: Liu
authors.forename: Xiao-Wei
authors.initials: XW
authors.lastname: Zhang
authors.forename: Yan-Biao
authors.initials: YB
authors.lastname: Kang
mesh_terms: D000577:Amides / Q000138:chemical synthesis* / Q000737:chemistry; D000605:Amino Alcohols / Q000138:chemical synthesis* / Q000737:chemistry*; D002384:Catalysis; D007555:Isoxazoles / Q000737:chemistry*; D015394:Molecular Structure; D010078:Oxazines / Q000737:chemistry*; D012428:Ruthenium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000577:Amides; D000605:Amino Alcohols; D007555:Isoxazoles; C441643:N-(3-hydroxy-1-hydroxymethyl-3-phenylpropyl)dodecanamide; D010078:Oxazines; D012428:Ruthenium