The truth about false unicorn (Chamaelirium luteum): Total synthesis of 23R,24S-Chiograsterol B defines the structure and stereochemistry of the major saponins from this medicinal herb

Matovic, Nicholas J., Stuthe, Julia M. U., Challinor, Victoria L., Bernhardt, Paul V., Lehmann, Reginald P., Kitching, William and De Voss, James J. (2011) The truth about false unicorn (Chamaelirium luteum): Total synthesis of 23R,24S-Chiograsterol B defines the structure and stereochemistry of the major saponins from this medicinal herb. Chemistry-A European Journal, 17 27: 7578-7591. doi:10.1002/chem.201100503


Author Matovic, Nicholas J.
Stuthe, Julia M. U.
Challinor, Victoria L.
Bernhardt, Paul V.
Lehmann, Reginald P.
Kitching, William
De Voss, James J.
Title The truth about false unicorn (Chamaelirium luteum): Total synthesis of 23R,24S-Chiograsterol B defines the structure and stereochemistry of the major saponins from this medicinal herb
Journal name Chemistry-A European Journal   Check publisher's open access policy
ISSN 0947-6539
Publication date 2011-06-27
Sub-type Article (original research)
DOI 10.1002/chem.201100503
Volume 17
Issue 27
Start page 7578
End page 7591
Total pages 4
Place of publication Germany
Publisher Wiley - V C H Verlag GmbH & Co. KGaA
Collection year 2012
Language eng
Abstract Chamaelirium luteum is used in traditional medicine systems and commercial botanical dietary supplements for the treatment of female reproductive health problems. Despite the wide use of this herb, only very limited phytochemical characterisation is available. Our investigation of C. luteum roots led to the isolation of two new steroidal saponins 1 and 2 that contain an unusual aglycone 3. The absolute configurations of these molecules were unable to be determined spectroscopically and thus the total synthesis of 3 was undertaken and achieved in 16 steps and 1.6 % overall yield from pregnenolone. The key step in the synthesis was the stereoselective installation of the side chain at C-17 and C-20, which employed anion-accelerated oxy-Cope methodology. The relative configuration of aglycone 3 was determined by X-ray crystallography of an advanced synthetic intermediate. The absolute configuration was based upon that of the pregnenolone-derived steroidal skeleton and determined to be 23R,24S.
Keyword Natural products
Rearrangement
Steroids
Structure elucidation
Synthesis design
Q-Index Code C1
Q-Index Status Confirmed Code
Institutional Status UQ

Document type: Journal Article
Sub-type: Article (original research)
Collections: Official 2012 Collection
School of Chemistry and Molecular Biosciences
 
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Created: Tue, 18 Oct 2011, 10:21:53 EST by Dr James De Voss on behalf of School of Chemistry & Molecular Biosciences