Identification of a Grain Beetle Macrolide Pheromone and Its Synthesis by Ring-Closing Metathesis Using a Terminal Alkyne.
Org Lett
; 17(20): 5004-7, 2015 Oct 16.
Article
em En
| MEDLINE
| ID: mdl-26406161
ABSTRACT
A major C18-macrolide was found during analysis of the frass of the storage beetle Oryzaephilus surinamensis to be (9Z,12Z,15R)-octadeca-9,12-dien-15-olide (10, cucujolide XI). The synthesis used ring-closing alkyne metathesis as a key step. The highly active 2,4,6-trimethylbenzylidyne molybdenum complex [MesCMo{OC(CF3)2Me}3] (12) allowed the use of a terminal alkyne and afforded the product in excellent yield. Bioassays proved the activity of the R-enantiomer 10 in the aggregation of the beetle. Cucujolide XI is the first macrolide pheromone oxidized at the ω-4 position.
Texto completo:
1
Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Feromônios
/
Besouros
/
Macrolídeos
/
Alcinos
Tipo de estudo:
Diagnostic_studies
Limite:
Animals
Idioma:
En
Ano de publicação:
2015
Tipo de documento:
Article