Determination of the absolute configuration of secondary alcohols by modified Horeau's method using HPLC

1989 ◽  
Vol 54 (1) ◽  
pp. 151-159 ◽  
Author(s):  
Aleš Svatoš ◽  
Irena Valterová ◽  
Anna Fábryová ◽  
Jan Vrkoč
Keyword(s):  
Absolute Configuration ◽  
Secondary Alcohols ◽  
Model Compounds ◽  
Defense Substance ◽  
Determination Of Absolute Configuration ◽  
The Absolute

A method for determination of absolute configuration of secondary alcohols, based on a modified Horeau's method, has been developed. The ratio of (1R,2'S)- and (1R,2'R)-N-[1-(1-naphthyl)-ethyl]-2-phenylbutanamides (V and VI, respectively) was determined by HPLC on a straight phase. The method was tested on a series of steroid and terpene model compounds and was used in the determination of absolute configuration of 15-ripperten-3α-ol (XV), the defense substance of Nasutitermes nigriceps termites. The sensibility of the determination is 100 nmol of the alcohol.

(-)-Strempeliopine, stereoselective total synthesis and the determination of absolute configuration

1986 ◽  
Vol 51 (8) ◽  
pp. 1731-1742 ◽  
Author(s):  
Josef Hájíček ◽  
Jan Trojánek
Keyword(s):  
Circular Dichroism ◽  
Total Synthesis ◽  
Absolute Configuration ◽  
Determination Of Absolute Configuration ◽  
Natural Base ◽  
The Absolute ◽  
Circular Dichroïsm

A synthesis of (±)-strempeliopine (II) is described, the key step of which is the stereoselective reductive rearrangement of 18-methylene-1,2-dehydroaspidospermidine (XI). The absolute configuration of the natural (-)-base II was determined as (2S, 7R, 20R, 21R) on the basis of its synthesis from (+)-18-methylenevincadifformine (XVII) the configuration of which was derived from a comparison of circular dichroism properties of bases with a β-anilinoacrylate chromophore. The biogenesis of the alkaloids of the schizozygane type is discussed.

ChemInform Abstract: Study for the Determination of the Absolute Configuration of Fluoromethylated Secondary Alcohols by the Modified Mosher Method.

ChemInform ◽  
2010 ◽  
Vol 28 (51) ◽  
pp. no-no
Author(s):  
L. XIAO ◽  
T. YAMAZAKI ◽  
T. KITAZUME ◽  
T. YONEZAWA ◽  
Y. SAKAMOTO ◽  
...  
Keyword(s):  
Absolute Configuration ◽  
Secondary Alcohols ◽  
The Absolute

A new approach for the determination of the absolute configuration of secondary alcohols by 1H NMR with O-substituted mandelate derivatives

1998 ◽  
Vol 39 (13) ◽  
pp. 1759-1762 ◽  
Author(s):  
Isabelle Chataigner ◽  
Jacques Lebreton ◽  
Didier Durand ◽  
André Guingant ◽  
Jean Villiéras
Keyword(s):  
1H Nmr ◽  
Absolute Configuration ◽  
Secondary Alcohols ◽  
New Approach ◽  
The Absolute

Determination of the absolute configuration of chiral secondary alcohols; new advances using 13C- and 2D-NMR spectroscopy

1993 ◽  
Vol 4 (7) ◽  
pp. 1527-1532 ◽  
Author(s):  
T. Pehk ◽  
E. Lippmaa ◽  
M. Lopp ◽  
A. Paju ◽  
B.C. Borer ◽  
...  
Keyword(s):  
Nmr Spectroscopy ◽  
Absolute Configuration ◽  
2D Nmr ◽  
Secondary Alcohols ◽  
2D Nmr Spectroscopy ◽  
The Absolute
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