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

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.

Enantioselective synthesis and determination of the absolute configuration of the male sex pheromone of the parasitoid wasp Urolepis rufipes

2020 ◽  
Vol 18 (18) ◽  
pp. 3463-3465 ◽  
Author(s):  
Kristina Melnik ◽  
Christopher Grimm ◽  
Johannes Wittbrodt ◽  
Joachim Ruther ◽  
Stefan Schulz
Keyword(s):  
Sex Pheromone ◽  
Absolute Configuration ◽  
Parasitoid Wasp ◽  
Enantioselective Synthesis ◽  
Male Sex Pheromone ◽  
Male Sex ◽  
The Absolute ◽  
Pheromonal Activity

The parasitoid wasp Urolepis rufipes uses terminally oxidized dihydrolinalool as a sex pheromone. The absolute configuration of the active enantiomer was established as 2S,6S by synthesis and its pheromonal activity was proven in a bioassay.

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