Determination of the absolute stereochemistry of chiral biphenanthryls in solution phase using chiroptical spectroscopic methods: 2,2′-Diphenyl-[3,3′-biphenanthrene]-4,4′-diol

Chirality ◽  
2008 ◽  
Vol 20 (3-4) ◽  
pp. 501-510 ◽  
Author(s):  
Ana G. Petrovic ◽  
Sarah E. Vick ◽  
Prasad L. Polavarapu
Keyword(s):  
Solution Phase ◽  
Spectroscopic Methods ◽  
The Absolute ◽  
Absolute Stereochemistry

Determination of the Absolute Stereochemistry of Cyclosmenospongine

2003 ◽  
Vol 66 (9) ◽  
pp. 1263-1265 ◽  
Author(s):  
Natalia K. Utkina ◽  
Vladimir A. Denisenko ◽  
Olga V. Scholokova ◽  
Aleksandra E. Makarchenko
Keyword(s):  
The Absolute ◽  
Absolute Stereochemistry

First synthesis and determination of the absolute stereochemistry of iso-cladospolide-B and cladospolides-B and C

2006 ◽  
Vol 47 (37) ◽  
pp. 6537-6540 ◽  
Author(s):  
G.V.M. Sharma ◽  
K. Laxmi Reddy ◽  
J. Janardhan Reddy
Keyword(s):  
The Absolute ◽  
Absolute Stereochemistry

scholarly journals Absolute Stereochemistry of the β-Hydroxy Acid Unit in Hantupeptins and Trungapeptins

2016 ◽  
Vol 11 (1) ◽  
pp. 1934578X1601100 ◽  
Author(s):  
Deepak Kumar Gupta ◽  
Gary Chi Ying Ding ◽  
Yong Chua Teo ◽  
Lik Tong Tan
Keyword(s):  
Amino Acid ◽  
Structural Feature ◽  
Absolute Configuration ◽  
Hydroxy Acid ◽  
Hplc Analysis ◽  
The Absolute ◽  
Absolute Stereochemistry ◽  
Common Structural Feature ◽  
Acid Unit

The β-hydroxy/amino acid unit is a common structural feature of many bioactive marine cyanobacterial depsipeptides. In this study, the absolute stereochemistry of the β-hydroxy acid moieties in hantupeptins and trungapeptins were determined through their synthesis and HPLC analysis of the Mosher ester derivatives. Synthesis of two3-hydroxy-2-methyloctanoic acid (Hmoa) stereoisomers, (2 S,3 R)-Hmoa and (2 S,3 S)-Hmoa, were achieved using diastereoselective asymmetric method and the retention times of all four Hmoa isomers were established indirectly by RPLC-MS analysis of their Mosher ester derivative standards. Based on the retention times of the standards, the absolute configuration of the Hmoa unit in hantupeptin C (3) and trungapeptin C (6) was assigned as (2 R,3 S)- and (2 S,3 R)-Hmoa, respectively. The use of the Mosher's reagents, coupled with HPLC analysis, provided a viable alternative to the absolute stereochemical determination of β-hydroxy acid units in depsipeptides.

scholarly journals Determination of the Absolute Stereochemistry of Limonene and α-Santalol by Raman Optical Activity Spectroscopy

2012 ◽  
Vol 7 (4) ◽  
pp. 1934578X1200700 ◽  
Author(s):  
Akira Sakamoto ◽  
Nao Ohya ◽  
Toshio Hasegawa ◽  
Hiroaki Izumi ◽  
Nakako Tokita ◽  
...  
Keyword(s):  
Organic Compounds ◽  
Optical Activity ◽  
Absolute Configuration ◽  
Natural Compounds ◽  
Vibrational Circular Dichroism ◽  
Raman Optical Activity ◽  
The Absolute ◽  
Circular Dichroïsm ◽  
Absolute Stereochemistry

Determining the absolute stereochemistry of organic compounds in solution remains a challenge. We investigated the use of Raman optical activity (ROA) spectroscopy to address this problem. The absolute configurations of (+)-( R)- and (-)-( S)-limonene were determined by ROA spectroscopy, which can be applied to smaller amounts of sample as compared with vibrational circular dichroism (VCD) spectroscopy. This ROA method was also applied to (+)-( E)-α-santalol and shown to be successful in the determination of the absolute configuration of this compound. ROA spectroscopy shows promise as a useful tool for determining the absolute stereochemistry of many natural compounds.

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