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

[img]PDF - Authorized users only
Language: English
147Kb
Title:Versatile Enantioselective Synthesis of Four Diastereomers of Serricornin, a Sex Pheromone of the Cigarette Beetle, Using the SAMP/RAMP-Hydrazone Method
Creators:
Job, Andreas
Nagelsdiek, René
Enders, Dieter
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 65, 4, pp. 524-538
Uncontrolled Keywords:Pheromones, Total synthesis, Hydrazones, Natural products, Reductions, Asymmetric synthesis

Abstract

Serricornin is a female-produced sex pheromone of the cigarette beetle (<i>Lasioderma serricorne</i>), which is a pest of dried foodstuffs and tobacco. We report a versatile and short synthesis of all possible 6,7-<i>syn</i>-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 (<i>R</i>)- and (<i>S</i>)-1-benzyloxy-2-methylpentan-3-one (<strong>4</strong>) and (2<i>S</i>,3<i>R</i>)- and (2<i>R</i>,3<i>S</i>)-1-iodo-3-(methoxy- methoxy)-2-methylpentane (<strong>9</strong>) were obtained. <p>

Title:Versatile Enantioselective Synthesis of Four Diastereomers of Serricornin, a Sex Pheromone of the Cigarette Beetle, Using the SAMP/RAMP-Hydrazone Method
Creators:
Job, Andreas
Nagelsdiek, René
Enders, Dieter
Uncontrolled Keywords:Pheromones, Total synthesis, Hydrazones, Natural products, Reductions, Asymmetric synthesis
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:65
Number:4
Page Range:pp. 524-538
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc20000524UNSPECIFIED
ID Code:1658
Item Type:Article
Deposited On:06 Feb 2009 17:11
Last Modified:06 Feb 2009 16:11

Citation

Job, Andreas; Nagelsdiek, René; Enders, Dieter (2000) Versatile Enantioselective Synthesis of Four Diastereomers of Serricornin, a Sex Pheromone of the Cigarette Beetle, Using the SAMP/RAMP-Hydrazone Method. Collection of Czechoslovak Chemical Communications, 65 (4). pp. 524-538. ISSN 0010-0765

Repository Staff Only: item control page