Tetrahedron, volume 46, issue 13-14, pages 4473-4486

A new synthesis of the four stereoisomers of 3,11-dimethyl-2-nonacosanone, the female-produced sex pheromone of the german cockroach

Publication type: Journal Article
Publication date: 1990-01-01
Journal: Tetrahedron
scimago Q3
wos Q2
SJR: 0.406
CiteScore: 3.9
Impact factor: 2.1
ISSN: 00404020, 14645416
Organic Chemistry
Drug Discovery
Biochemistry
Abstract
The pure four stereoisomers of 3,ll-dimethyl-2-nonacosanone (1), the female-produced sex pheromone of the German cockroach, were synthesized starting from ( R )-citronellol ( 2 a) and ethyl ( R )-3-hydroxybutanoate ( 3 ). The key step was the chromatographic separation of (5RS,6R)-6-hydroxy-5-methyl-2-heptanone ( 16 a) to give pure ( 5R,6R - and) 5S,6R -isomers. All of the four stereoisomers of 1 were bioactive.
Found 
Found 

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