Determination of the absolute configuration of picrasidine Y, a naturally occurring β-carboline alkaloid

Kazuo Koike, Hiroshi Yoshino, Hong Yu Li, Tatsunori Sasaki, Wei Li

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Abstract

Abstract The absolute configuration of picrasidine Y, a β-carboline alkaloid isolated from Picrasma quassioides (Simaroubaceae), has not been determined. To determine the absolute configuration of picrasidine Y, we synthesized stereoisomers of picrasidine Y through 7-step chemical reactions using tartaric acid as a starting material. Moreover, we extended the scope of application of this synthetic method to canthin-5,6-dione compounds. The absolute configuration of natural picrasidine Y was elucidated based on comparisons of chemically synthesized isoforms with the naturally occurring compound in 1H and 13C NMR spectra, specific optical rotation, HPLC analysis with chiral columns, computational molecular simulation, and analysis with the CD exciton chirality method.

Original languageEnglish (US)
Article number46568
Pages (from-to)5306-5308
Number of pages3
JournalTetrahedron Letters
Volume56
Issue number38
DOIs
Publication statusPublished - Sep 16 2015

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Keywords

  • Absolute configuration
  • Canthin-5,6-dione
  • Picrasidine Y
  • Picrasma
  • β-Carboline alkaloid

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

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