Stereoselective synthesis of the obscure mealybug pheromone by hydrogenation of a tetrasubstituted alkene precursor

An improved diastereoselective synthesis of (1R∗,2R∗,3S∗)-1-acetoxymethyl-2,3,4,4-tetramethylcyclopentane 1, the sex pheromone of the obscure mealybug, Pseudococcus viburni, is described. The key step was diastereoselective catalytic hydrogenation of the tetrasubstituted double bond in 2,3,4,4-tetra...

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Bibliographic Details
Published inTetrahedron letters Vol. 52; no. 32; pp. 4224 - 4226
Main Authors Zou, Yunfan, Millar, Jocelyn G.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 10.08.2011
Elsevier
Subjects
Alicyclic compounds
Alicyclic compounds, terpenoids, prostaglandins, steroids
Bonding
Catalysis
Catalytic hydrogenation
Chemistry
Chemistry, Organic
Diastereoselective synthesis
Exact sciences and technology
Hydrogenation
Monoterpenoid
Olefins
Organic chemistry
Pheromone
Physical Sciences
Precursors
Preparations and properties
Pseudococcus
Science & Technology
Sex
Synthesis (chemistry)
Terpenoids
Tetrahedrons
Pheromone
Monoterpenoid
Diastereoselective synthesis
Catalytic hydrogenation
DIASTEREOSELECTIVE PROTONATION
CYCLOPENTENONES
SEX-PHEROMONE
Terpenoid
Sex pheromone
Catalytic reaction
Hydrogenation
Diastereoselectivity
Stereoselectivity
Alkene
Monoterpene
Chemical synthesis
Ethylenic compound
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Summary:An improved diastereoselective synthesis of (1R∗,2R∗,3S∗)-1-acetoxymethyl-2,3,4,4-tetramethylcyclopentane 1, the sex pheromone of the obscure mealybug, Pseudococcus viburni, is described. The key step was diastereoselective catalytic hydrogenation of the tetrasubstituted double bond in 2,3,4,4-tetramethyl-cyclopent-2-enone 4 to give the thermodynamically less favored cis-2,3,4,4-tetramethyl-cyclopentanone 3a.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2011.06.030