Absolute Configuration of Actinophyllic Acid As Determined through Chiroptical Data
Journal of Natural Products2009Vol. 72(3), pp. 430–432
Citations Over TimeTop 12% of 2009 papers
Abstract
The absolute configuration of actinophyllic acid (-)-1, an alkaloid with an unprecedented 2,3,6,7,9,13c-hexahydro-1H-1,7,8-(methanetriyloxymethano)pyrrolo[1',2':1,2]azacino[4,3-b]indole-8(5H)-carboxylic acid skeleton isolated from Alstonia actinophylla, was determined through the study of its corresponding methyl ester 2. Racemic 2 was separated into (+)-2 and (-)-2 enantiomers, and they were assigned unambiguously as 15S,16R,19R,20R,21S and 15R,16S,19S,20S,21R, respectively, by the use of optical rotation and electronic circular dichroism. Finally, (-)-2 was characterized as the methyl ester of naturally occurring (-)-1. The assigned 15R,16S,19S,20S,21R-configuration of (-)-1 is consistent with a proposed biosynthetic pathway.
Related Papers
- → Assignment of the Absolute Configuration of Concentricolide – Absolute Configuration Determination of Its Bioactive Analogs Using DFT Methods(2009)37 cited
- → On the Absolute Configuration of Chiral 1,4-Dihydropyridazines Synthesized by Organocatalysed Reactions(2013)9 cited
- → On the Absolute Configuration of Schweinfurthinol(2011)3 cited
- Theoretical methods in configuration determinations for natural chiral products:research advances(2015)
- → The determination of the absolute configuration of tri-o-thymotide by crystal structure analysis and optical rotation.(1979)16 cited