The First Nonempirical Circular Dichroism Determination of the Absolute Configuration ofN-Phthalimidosulfoximines Based on Exciton Coupling Mechanism and a Correlation with the Absolute Configuration of Chiral Sulfoxides

2003 ◽  
Vol 68 (25) ◽  
pp. 9821-9822 ◽  
Author(s):  
Jacek Gawroński ◽  
Jakub Grajewski ◽  
Józef Drabowicz ◽  
Marian Mikołajczyk
Keyword(s):  
Circular Dichroism ◽  
Absolute Configuration ◽  
Coupling Mechanism ◽  
Exciton Coupling ◽  
Chiral Sulfoxides ◽  
The Absolute ◽  
Circular Dichroïsm

scholarly journals Vibrational Circular Dichroism: Recent Advances for the Assignment of the Absolute Configuration of Natural Products

2015 ◽  
Vol 10 (10) ◽  
pp. 1934578X1501001 ◽  
Author(s):  
Eleuterio Burgueño-Tapia ◽  
Pedro Joseph-Nathan
Keyword(s):  
Natural Products ◽  
Circular Dichroism ◽  
Absolute Configuration ◽  
Aromatic Compounds ◽  
Vibrational Circular Dichroism ◽  
Exciton Coupling ◽  
Coupling Approach ◽  
The Absolute ◽  
Circular Dichroïsm

Vibrational circular dichroism (VCD) emerged during the last decade as a reliable tool for the absolute configuration (AC) determination of organic compounds. The principles, instrumentation, and methodology applied prior to early 2013 were recently reviewed by us. Since VCD is a very dynamic field, the aim of this review is to update VCD advances for the AC assignment of terpenoids, aromatic compounds, alkaloids, and other natural products for the 2013-2014 period, when VCD was applied to the AC assignment of some 70 natural products. In addition, although discovered in 2012, a brief introduction to the VCD exciton coupling approach and its applications in natural products AC assignment is presented.

Vibrational Circular Dichroism (VCD), VCD Exciton Coupling, and X-ray Determination of the Absolute Configuration of an α ,β -Unsaturated Germacranolide

Chirality ◽  
2015 ◽  
Vol 27 (3) ◽  
pp. 247-252 ◽  
Author(s):  
Mariano Sánchez-Castellanos ◽  
María A. Bucio ◽  
Angelina Hernández-Barragán ◽  
Pedro Joseph-Nathan ◽  
Gabriel Cuevas ◽  
...  
Keyword(s):  
Circular Dichroism ◽  
Absolute Configuration ◽  
Vibrational Circular Dichroism ◽  
X Ray ◽  
Exciton Coupling ◽  
The Absolute ◽  
Circular Dichroïsm

scholarly journals Vibrational Circular Dichroism: Recent Advances for the Assignment of the Absolute Configuration of Natural Products

2017 ◽  
Vol 12 (5) ◽  
pp. 1934578X1701200 ◽  
Author(s):  
Eleuterio Burgueño-Tapia ◽  
Pedro Joseph-Nathan
Keyword(s):  
Natural Products ◽  
Circular Dichroism ◽  
Absolute Configuration ◽  
Aromatic Compounds ◽  
Vibrational Circular Dichroism ◽  
Exciton Coupling ◽  
Coupling Approach ◽  
The Absolute ◽  
Circular Dichroïsm

Vibrational circular dichroism (VCD) emerged during the last decade as a reliable tool for the absolute configuration (AC) determination of organic compounds. The principles, instrumentation, and methodology applied prior to early 2013 were recently reviewed by us. Since VCD is a very dynamic field, the aim of this review is to update VCD advances for the AC assignment of terpenoids, aromatic compounds, alkaloids, and other natural products for the 2013–2014 period, when VCD was applied to the AC assignment of some 70 natural products. In addition, although discovered in 2012, a brief introduction to the VCD exciton coupling approach and its applications in natural products AC assignment is presented.

(-)-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.

Absolute configuration determination of theanti-head-to-head photocyclodimer of anthracene-2-carboxylic acid through cocrystallization withL-prolinol

2013 ◽  
Vol 69 (11) ◽  
pp. 1411-1413 ◽  
Author(s):  
Yuko Kawanami ◽  
Hidekazu Tanaka ◽  
Jun-ichi Mizoguchi ◽  
Nobuko Kanehisa ◽  
Gaku Fukuhara ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Circular Dichroism ◽  
Carboxylic Acid ◽  
Absolute Configuration ◽  
Void Space ◽  
Circular Dichroism Spectra ◽  
The Absolute ◽  
Circular Dichroïsm ◽  
Hydrogen Bonded

The absolute configuration has been established of the enantiopureanti-head-to-head cyclodimer of anthracene-2-carboxylic acid (AC) cocrystallized with L-propinol and dichloromethane [systematic name: (S)-2-(hydroxymethyl)pyrrolidin-1-ium (5R,6S,11R,12S)-8-carboxy-5,6,11,12-tetrahydro-5,12:6,11-bis([1,2]benzeno)dibenzo[a,e][8]annulene-2-carboxylate dichloromethane monosolvate], C5H12NO+·C30H19O4−·CH2Cl2. In the crystal structure, the AC dimer interacts with L-prolinol through a nine-membered hydrogen-bonded ring [R22(9)], while the dichloromethane molecule is incorporated to fill the void space. The absolute configuration determined in this study verifies a recent assignment made by comparing theoreticalversusexperimental circular dichroism spectra.

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