Stereoselective Synthesis of a Ceramide Transporter Protein (CERT)-Dependent Ceramide-Trafficking Inhibitor, (1R,3S)-HPA-12, via Gold(I)-Catalyzed Cyclization of a Propargylic N-Hydroxylamine

Bandari Chandrasekhar, Sewon Ahn, Jae Sang Ryu

Research output: Contribution to journalArticlepeer-review

5 Scopus citations

Abstract

A ceramide transporter protein (CERT)-dependent ceramide-trafficking inhibitor, HPA-12, is efficiently synthesized using gold(I)-catalyzed cyclization of a propargylic N-hydroxylamine, which is prepared via a stereoselective nitrone-alkyne addition reaction. The resulting 4-isoxazoline is converted into a syn-1,3-amino alcohol through stereoselective reduction and reductive ring opening.

Original languageEnglish
Article numberss-2016-f0702-op
Pages (from-to)1569-1574
Number of pages6
JournalSynthesis (Germany)
Volume49
Issue number7
DOIs
StatePublished - 1 Apr 2017

Keywords

  • 4-isoxazoline
  • gold
  • HPA-12
  • nitrone
  • stereoselective synthesis

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