An approach to the synthesis and attachment of scillabiose to steroids

Filip S. Ekholm, Gyula Schneider, János Wölfling, Reko Leino

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

Hellebrin and transvaalin are two naturally occurring saponins with biological activity. In the present paper, we describe a high yielding route to the synthesis and coupling of their shared glycone, scillabiose, to a model steroid. A convergent coupling strategy utilizing a scillabiose-based glycosyl donor was devised for the glycosylation. This convergent approach is appealing due to its high efficiency and simple deprotection procedure and may find further use in total synthesis of naturally occurring saponins and related compounds sharing the same glycone. Due to the widespread occurrence of this glycone in nature, the complete NMR spectroscopic characterization of all compounds prepared herein is provided as reference material. In addition, glycosylations were performed with the monosaccharide constituents of scillabiose, thereby providing a limited series of glycosylated steroids for potential future evaluation of the effects of the glycone on the overall biological activity.

Original languageEnglish
Pages (from-to)588-595
Number of pages8
JournalSteroids
Volume76
Issue number6
DOIs
Publication statusPublished - May 1 2011

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Keywords

  • Androst-5-en-3β-ol-17-one
  • Carbohydrates
  • Glycosylation
  • NMR spectroscopy
  • Saponins
  • Scillabiose

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Endocrinology
  • Pharmacology
  • Clinical Biochemistry
  • Organic Chemistry

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