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A New Synthesis of the Four Stereoisomers of 3,11-Dimethyl-2-nonacosanone, the Female-produced Sex Pheromone of the German Cockroach by Kenji Mori; Hirosato Takikawa is a Chemistry article available to read on EtoBox.
What is A New Synthesis of the Four Stereoisomers of 3,11-Dimethyl-2-nonacosanone, the Female-produced Sex Pheromone of the German Cockroach about?
## Abslt'M - The pure four stereoisomers of 3,11-dimethyl-Znonacosanone (I), the female-produced sex pheromone of the German cockroach, were synthesized starting from (/I)-citronehol (ul) and ethyl (R)-3-hydroxybutanoate (3). The key step was the chromatographic separation of (SRS,6R)-6-hydroxy-5-methyl-2-heptanone (168) to give pure (SF?,6R)-and (5S,6R)-isomers. Au of the four stereoisomers of 1 were bioactive. 3,11-Dimethyl-Znonacosanone (1) was isolated by Niida et a/ in 1975 as the female-produced sex pheromone of the German cockroach, B/attella germanica. Upon contact with antennae, it elicits wing-raising and direction-turning response from the male aduIts.'y2 Our synthesis of its four stereoisomers in 1978 enabled us to assign (3S,ll.$stereochemistry to the natural pheromone.3s4 Bioassay of these four stereoisomers of 1 showed them to be equally bioactive? In our previous synthesis of 1, however, the enantiomeric purity of the starting (R)-citronehic acid was only 92% e.e.4 Although the stereoisomers of 1 could be purified by recrystallization, they might have been enantiomericahy impure. In order to obtain conchtsive evidence with regard to the non-stereoselective nature of
Who reads A New Synthesis of the Four Stereoisomers of 3,11-Dimethyl-2-nonacosanone, the Female-produced Sex Pheromone of the German Cockroach?
It is typically read by researchers, students, and practitioners in Chemistry.
- Author
- Kenji Mori; Hirosato Takikawa
- Publisher
- Elsevier Science; Elsevier ; Elsevier Ltd.; Elsevier BV (ISSN 0040-4020)
- Published
- 1990
- Language
- EN
- Field
- Chemistry (Physical Sciences)