Synthesis and circular dichroism studies of N,N-bis(2-quinolylmethyl)amino acid Cu(II) complexes: Determination of absolute configuration and enantiomeric excess by the exciton coupling method

Chirality ◽  
2002 ◽  
Vol 14 (6) ◽  
pp. 471-477 ◽  
Author(s):  
Andrea E. Holmes ◽  
Steffen Zahn ◽  
James W. Canary
Keyword(s):  
Circular Dichroism ◽  
Amino Acid ◽  
Absolute Configuration ◽  
Enantiomeric Excess ◽  
Coupling Method ◽  
Exciton Coupling ◽  
Determination Of Absolute Configuration ◽  
Circular Dichroïsm

(-)-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.

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