Absolute Configuration Determination of Retroflexanone Using the Advanced Mosher Method and Application of HPLC-NMR

Caleb Singleton; Robert Brkljača; Sylvia Urban

doi:10.3390/md16060205

Absolute Configuration Determination of Retroflexanone Using the Advanced Mosher Method and Application of HPLC-NMR

Mar Drugs. 2018 Jun 12;16(6):205. doi: 10.3390/md16060205.

Authors

Caleb Singleton¹, Robert Brkljača², Sylvia Urban³

Affiliations

¹ School of Science (Applied Chemistry and Environmental Science), RMIT University, GPO Box 2476, Melbourne, VIC 3001, Australia. caleb.taicho@gmail.com.
² School of Science (Applied Chemistry and Environmental Science), RMIT University, GPO Box 2476, Melbourne, VIC 3001, Australia. robert.brkljaca@rmit.edu.au.
³ School of Science (Applied Chemistry and Environmental Science), RMIT University, GPO Box 2476, Melbourne, VIC 3001, Australia. sylvia.urban@rmit.edu.au.

Abstract

The absolute configuration of retroflexanone (1) and a closely related phlorogluinol (2) was established using the advanced Mosher method and by application of HPLC-NMR. HPLC-NMR permitted a small scale Mosher method analysis to be carried out on these unstable phloroglucinols.

Keywords: HPLC-NMR; Mosher; phloroglucinol; retroflexanone; secondary alcohol.

MeSH terms

Chromatography, High Pressure Liquid / methods
Magnetic Resonance Spectroscopy / methods
Molecular Structure
Phaeophyceae / chemistry*
Phloroglucinol / analogs & derivatives*
Phloroglucinol / analysis
Phloroglucinol / chemistry*
Stereoisomerism

Substances

retroflexanone
Phloroglucinol