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

ChemInform ◽  
2000 ◽  
Vol 31 (39) ◽  
pp. no-no
Author(s):  
Andreas Job ◽  
Rene Nagelsdiek ◽  
Dieter Enders
Keyword(s):  
Sex Pheromone ◽  
Enantioselective Synthesis ◽  
Cigarette Beetle

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

A practical enantioselective synthesis of the cigarette beetle sex pheromone serricornin

Tetrahedron ◽  
1994 ◽  
Vol 50 (9) ◽  
pp. 2703-2714 ◽  
Author(s):  
Philip C.-M. Chan ◽  
J.Michael Chong ◽  
Karim Kousha
Keyword(s):  
Sex Pheromone ◽  
Enantioselective Synthesis ◽  
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.

Enantioselective Synthesis of the Sex Pheromone of Lichen Moth, Miltochrista calamine, and Its Diastereomer

Synlett ◽  
2021 ◽  
Author(s):  
Jiangchun Zhong ◽  
Gucheng Yuan ◽  
Jiawei Liu ◽  
Shihang Yu ◽  
Xueyang Wang ◽  
...  
Keyword(s):  
Sex Pheromone ◽  
Enantioselective Synthesis ◽  
Synthetic Approach ◽  
Chiral Auxiliaries ◽  
Synthetic Sex Pheromone ◽  
Key Steps

AbstractThe synthesis of a Miltochrista calamine sex pheromone and its diastereomer has been developed. The key steps of the synthetic approach involved Evans’ chiral auxiliaries and the addition of alkyne to aldehyde, which were firstly applied to prepare this sex pheromone and its diastereomer. The synthetic sex pheromone could be used to trap insects and study physiological and ecological questions of the lichen moth.

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