CD-Spectroscopic Investigations for the Determination of the Absolute Configuration of (4R,6S,7S)-Serricomin

2001 ◽  
Vol 56 (12) ◽  
pp. 1344-1348 ◽  
Author(s):  
Jörg Fleischhauer ◽  
Sven Gabriel ◽  
Dieter Enders ◽  
Axe Wollmer
Keyword(s):  
Sex Pheromone ◽  
Total Synthesis ◽  
Absolute Configuration ◽  
Lasioderma Serricorne ◽  
Cigarette Beetle ◽  
Spectroscopic Investigations ◽  
The Absolute ◽  
Circular Dichroïsm ◽  
Rotational Strengths

Abstract The absolute configuration of the conformationally flexible (4R,6S,7S)-serricornin, a non­ natural isomer of the female-produced sex pheromone of the cigarette beetle (Lasioderma serricorne), was determined by comparison of measured and calculated circular dichroism spectra. The rotational strengths were calculated by means of the semiempirical CNDO/2S-method. The total synthesis was accomplished by the SAMP/RAMP-hydrazone method.

(-)-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.

Determination of the absolute configuration at C-6 and C-7 of serricornin (4,6-dimethyl-7-hydroxy-3-nonanone), the sex pheromone of the cigarette beetle

1981 ◽  
Vol 22 (12) ◽  
pp. 1127-1130 ◽  
Author(s):  
Kenji Mori ◽  
Hiroko Nomi (née Iwasawa) ◽  
Tatsuji Chuman ◽  
Masahiro Kohno ◽  
Kunio Kato ◽  
...  
Keyword(s):  
Sex Pheromone ◽  
Absolute Configuration ◽  
Cigarette Beetle ◽  
The Absolute

Asymmetric Total Synthesis and Determination of the Absolute Configuration of (+)-Srilankenyne via Sequence-Sensitive Halogenations Guided by Conformational Analysis

2021 ◽  
Vol 23 (4) ◽  
pp. 1321-1326
Author(s):  
Hongjun Jang ◽  
Soo Yeon Kwak ◽  
Dongjoo Lee ◽  
Juan V. Alegre-Requena ◽  
Hyoungsu Kim ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Conformational Analysis ◽  
Absolute Configuration ◽  
Asymmetric Total Synthesis ◽  
The Absolute

Total synthesis and determination of the absolute configuration of (−)-longilene peroxide

2001 ◽  
Vol 42 (36) ◽  
pp. 6307-6309 ◽  
Author(s):  
Yoshiki Morimoto ◽  
Toshiyuki Iwai ◽  
Takamasa Kinoshita
Keyword(s):  
Total Synthesis ◽  
Absolute Configuration ◽  
The Absolute

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.

First Total Synthesis and Determination of the Absolute Configuration of Strictifolione, a New 6-(ω-Phenylalkenyl)-5,6-dihydro-α-pyrone, Isolated from Cryptocarya strictifolia.

ChemInform ◽  
2003 ◽  
Vol 34 (7) ◽  
Author(s):  
Lia Dewi Juliawaty ◽  
Yoshimi Watanabe ◽  
Mariko Kitajima ◽  
Sjamsul Arifin Achmad ◽  
Hiromitsu Takayama ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Absolute Configuration ◽  
The Absolute

ChemInform Abstract: Total Synthesis and Determination of the Absolute Configuration of FD-838, a Naturally Occurring Azaspirobicyclic Product.

ChemInform ◽  
2009 ◽  
Vol 40 (47) ◽  
Author(s):  
Yujiro Hayashi ◽  
Kuppusamy Sankar ◽  
Hayato Ishikawa ◽  
Yuriko Nozawa ◽  
Kazutoshi Mizoue ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Absolute Configuration ◽  
Naturally Occurring ◽  
The Absolute
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