Stereospecific Synthesis of Two Isomers of (4,8) - Dimethyldecanal: The Aggregation Pheromone of Tribolium spp



Document title: Stereospecific Synthesis of Two Isomers of (4,8) - Dimethyldecanal: The Aggregation Pheromone of Tribolium spp
Journal: Journal of the Brazilian Chemical Society
Database: PERIÓDICA
System number: 000310759
ISSN: 0103-5053
Authors: 1
2
3
Institutions: 1Universidade Federal do Parana, Departamento de Quimica, Curitiba, Parana. Brasil
2Universidade Federal de Uberlandia, Departamento de Quimica, Uberlandia, Minas Gerais. Brasil
3Universidade Federal de Sao Carlos, Departamento de Quimica, Sao Carlos, Sao Paulo. Brasil
Year:
Season: Sep
Volumen: 9
Number: 5
Pages: 511-513
Country: Brasil
Language: Inglés
Document type: Artículo
Approach: Experimental
English abstract A straightforward stereospecific synthesis of two stereoisomers, (4R, 8S) and (4S, 8S), of 4,8-dimethyldecanal (1), out of four possible isomers, is described. The key step employs the coupling reaction of tosylates (3) and (3a), which are obtained from (R)- and (S)- citronellol, with the chiral Grignard reagent prepared from comercial (S)-(+)-1-bromo-2-methylbutane (4)
Portuguese abstract Uma síntese estereoespecífica para dois estereoisômeros, (4R, 8S) e (4S, 8S), do 4,8-dimetildecanal (1), entre os quatro possíveis, é descrita em apenas três etapas. A etapa chave emprega a reação de acoplamento dos tosilatos (3) e (3a), obtidos do (R)- e (S)-citronelol, com o reagente de Grignard preparado a partir do (S)-(+)-1-bromo-2-metilbutano (4) comercial
Disciplines: Química,
Biología
Keyword: Química orgánica,
Insectos,
Feromonas,
Síntesis asimétrica,
4,8-dimetildecanal,
Isómeros,
Tribolium
Keyword: Chemistry,
Biology,
Organic chemistry,
Insects,
Pheromones,
Asymmetric synthesis,
4,8-dimethyldecanal,
Isomers,
Tribolium
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