Stereoselective synthesis of (+)-polyoxamic acid starting with a chiral aziridine

Hojong Yoon, Taebo Sim

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

An efficient and stereoselective synthesis of (+)-polyoxamic acid was developed. The route starts with the commercially available 1-(R)-α- methylbenzylaziridine-2-methanol, a substance that has not been used previously as a starting material for the preparation of this target. The route also features the use of a stereocontrolled Sharpless asymmetric dihydroxylation reaction, promoted by AD-mix-α, which is followed by a regioselective aziridine ring-opening process, to generate the basic skeleton of target natural product. Subsequent oxidation and global deprotection produces (+)-polyoxamic acid.

Original languageEnglish
Pages (from-to)3276-3280
Number of pages5
JournalSynthesis (Germany)
Volume45
Issue number23
DOIs
Publication statusPublished - 2013 Sep 27

Fingerprint

Acids
Biological Products
Methanol
Oxidation
aziridine
polyoxamic acid

Keywords

  • (+)-polyoxamic acid
  • asymmetric dihydroxylation
  • chiral aziridine
  • natural product synthesis
  • polyhydroxylated amino acid

ASJC Scopus subject areas

  • Organic Chemistry
  • Catalysis

Cite this

Stereoselective synthesis of (+)-polyoxamic acid starting with a chiral aziridine. / Yoon, Hojong; Sim, Taebo.

In: Synthesis (Germany), Vol. 45, No. 23, 27.09.2013, p. 3276-3280.

Research output: Contribution to journalArticle

Yoon, Hojong ; Sim, Taebo. / Stereoselective synthesis of (+)-polyoxamic acid starting with a chiral aziridine. In: Synthesis (Germany). 2013 ; Vol. 45, No. 23. pp. 3276-3280.
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