Pheromone synthesis. Part 243: Synthesis and biological evaluation of (3R,13R,1′S)-1′-ethyl-2′-methylpropyl 3,13-dimethylpentadecanoate, the major component of the sex pheromone of Paulownia bagworm, Clania variegata, and its stereoisomers

Autor:	Ashraf M. El-Sayed, Takuya Tashiro, David M. Suckling, Boguang Zhao, Kenji Mori
Rok vydání:	2010
Předmět:	Stereochemistry Chemistry Monoterpene Organic Chemistry Metathesis Biochemistry Chemical synthesis chemistry.chemical_compound Sex pheromone Drug Discovery Wittig reaction Citronellal Pheromone Organic chemistry 2-Methyl-3-pentanol
Zdroj:	Tetrahedron. 66:2642-2653
ISSN:	0040-4020
Popis:	All of the four stereoisomers of (1′S)-1′-ethyl-2′-methylpropyl 3,13-dimethylpentadecanoate, the major component of the female sex pheromone of Clania variegata, were synthesized by employing olefin cross metathesis as the key reaction and starting from (R)- or (S)-2-methyl-1-butanol, (R)- or (S)-citronellal, and (S)-2-methyl-3-pentanol. Their bioassay revealed the (3R,13R,1′S)-isomer as the bioactive one, whose more efficient synthesis was achieved in two different ways by employing Wittig reaction as the key step.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::e308d5fe480c4af1838ab195bea0b95a https://doi.org/10.1016/j.tet.2010.02.028 Zobrazit plný text záznamu Full Text from ScienceDirect