Synthesis of the Sex Pheromone of the Oleander Scale (Aspidiotus nerii)

Autor:	Mary Cecilia Montaño Castañeda, Jaime Primo, Marzo Bargués Javier, Navarro Fuertes Ismael
Rok vydání:	2019
Předmět:	Hemiptera Aspidiotus nerii Molecular Structure Chemistry Stereochemistry Sex pheromone Organic Chemistry Animals Sex Attractants
Zdroj:	The Journal of Organic Chemistry. 84:8578-8588
ISSN:	1520-6904 0022-3263
DOI:	10.1021/acs.joc.9b01001
Popis:	A total synthesis of the oleander scale [ Aspidiotus nerii (Bouche)] sex pheromone, the unique sesquiterpenoid containing a cyclobutane moiety of this class of compounds, has been developed. In order to implement this sex pheromone as a new environmentally friendly tool to manage this pest, a more cost-effective, multigram synthesis was required. This new synthetic route, having a Blaise reaction, iron-catalyzed carbon-carbon coupling, and [2 + 2] photocycloaddition reactions as key steps, provides a general access to 4-alkyl lactones as well as a robust access to the target sex pheromone. Starting from readily available compounds as 3-hydroxypropanenitrile, ethyl bromoacetate, and 2-acetyl butyrolactone, the synthetic sequence afforded the A. nerii sex pheromone with minimum intermediate purification and good overall yield in nine linear steps.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::acf4a5eb1b1a83e76b62faf6f35dbb0f https://doi.org/10.1021/acs.joc.9b01001 Zobrazit plný text záznamu