Preparation of aminosaccharides using ester-imine condensations: syntheses of methyl N-benzoylacosaminide and methyl N-[oxo(phenylmethoxy) acetyl)daunosaminide from (S)-ethyl 3-hydroxybutyrate

Judith C. Gallucci, Deok Chan Ha, David J. Hart

Research output: Contribution to journalArticle

25 Citations (Scopus)

Abstract

The dianion of (S)-ethyl β-hydroxybutyrate (1) was treated with N-trimethylsilyl Imine 2 to afford β-lactam 4. The same dianion reacted with N-ary1 imine 10 to give β-lactams 11, 12, and 13. A three-step sequence was used to convert 4 into the β-lactam-pyran hybrid 9 while a five-step sequence was developed to transform 11 and 12 into 9. Application of the carboxyinversion reaction to derivatives of 9 afforded protected analogs of the amino-saccharldes daunosamlne (5) and acosamine (6).

Original languageEnglish
Pages (from-to)1283-1292
Number of pages10
JournalTetrahedron
Volume45
Issue number5
DOIs
Publication statusPublished - 1989
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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