Enantioselective synthesis of (−)-serricornin, a sex pheromone of a female cigarette beetle (Lasioderma serricorne F.)

1993 ◽  
Vol 4 (7) ◽  
pp. 1573-1578 ◽  
Author(s):  
Masaaki Miyashita ◽  
Yuuko Toshimitsu ◽  
Tomonori Shiratani ◽  
Hiroshi Irie
Keyword(s):  
Sex Pheromone ◽  
Enantioselective Synthesis ◽  
Lasioderma Serricorne ◽  
Cigarette Beetle

Versatile Enantioselective Synthesis of Four Diastereomers of Serricornin, a Sex Pheromone of the Cigarette Beetle, Using the SAMP/RAMP-Hydrazone Method

2000 ◽  
Vol 65 (4) ◽  
pp. 524-538 ◽  
Author(s):  
Andreas Job ◽  
René Nagelsdiek ◽  
Dieter Enders
Keyword(s):  
Sex Pheromone ◽  
Enantioselective Synthesis ◽  
Starting Material ◽  
Lasioderma Serricorne ◽  
Diethyl Ketone ◽  
Cigarette Beetle ◽  
Stereogenic Centers ◽  
Short Synthesis ◽  
Derivatives Of

Serricornin is a female-produced sex pheromone of the cigarette beetle (Lasioderma serricorne), which is a pest of dried foodstuffs and tobacco. We report a versatile and short synthesis of all possible 6,7-syn-isomers of serricornin, including the natural isomer. Starting from the SAMP and RAMP derivatives of diethyl ketone we obtained four different enantiopure and diastereomerically pure serricornins. The main advantage of this method is that only a single kind of chiral starting material is needed for the construction of three stereogenic centers. During the synthesis further useful intermediates including (R)- and (S)-1-benzyloxy-2-methylpentan-3-one (4) and (2S,3R)- and (2R,3S)-1-iodo-3-(methoxy- methoxy)-2-methylpentane (9) were obtained.

Olfactory responses to the sex pheromone component and its behavioural inhibitor in the male cigarette beetle, Lasioderma serricorne

1992 ◽  
Vol 38 (9) ◽  
pp. 705-709 ◽  
Author(s):  
Kentaro Okada ◽  
Akihiko Watanabe ◽  
Masataka Mori ◽  
Kazuko Shimazaki ◽  
Tatsuji Chuman ◽  
...  
Keyword(s):  
Sex Pheromone ◽  
Pheromone Component ◽  
Lasioderma Serricorne ◽  
Cigarette Beetle ◽  
Olfactory Responses

scholarly journals Fine Structure of Antennal Sex-Pheromone-Sensitive Sensilla of the Male Cigarette Beetle, Lasioderma serricorne(Coleoptera:Anobiidae)

1993 ◽  
Vol 28 (3) ◽  
pp. 283-289 ◽  
Author(s):  
Kentaro OKADA ◽  
Akihiko WATANABE ◽  
Masataka MORI ◽  
Kazuko SHIMAZAKI ◽  
Yoshisuke NISHI ◽  
...  
Keyword(s):  
Fine Structure ◽  
Sex Pheromone ◽  
Lasioderma Serricorne ◽  
Cigarette Beetle

scholarly journals Activity of stereoisomers of serricornin, sex pheromone of the cigarette beetle (Lasioderma serricorne F.).

1984 ◽  
Vol 48 (11) ◽  
pp. 2833-2834 ◽  
Author(s):  
Keiko MOCHIZUKI ◽  
Tatsuji CHUMAN ◽  
Masataka MORI ◽  
Masahiro KOHNO ◽  
Kunio KATO
Keyword(s):  
Sex Pheromone ◽  
Lasioderma Serricorne ◽  
Cigarette Beetle

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.

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