Determination of the absolute configuration of picrasidine Y, a naturally occurring β-carboline alkaloid. Issue 38 (16th September 2015)

• Record Type: Journal Article
• Authors: Koike, Kazuo; Yoshino, Hiroshi; Li, Hong-yu; Sasaki, Tatsunori; Li, Wei
• Is Part Of: Tetrahedron letters. Volume 56:Issue 38(2015)
• Page Start: 5306
• Page End: 5308
• Publication Date: 2015-09-16
• Subjects: Absolute configuration -- Picrasidine Y -- β-Carboline alkaloid -- Canthin-5, 6-dione -- Picrasma; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2015.07.079
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical 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 1 H and 13 C NMR spectra, specific optical rotation, HPLC analysis with chiral columns, computational molecular simulation, and analysis with the CD exciton chirality method.