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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| Published in | Tetrahedron letters Vol. 52; no. 32; pp. 4224 - 4226 |
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| Main Authors | , |
| Format | Journal Article |
| Language | English |
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Elsevier Ltd
10.08.2011
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| Abstract | 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. |
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| AbstractList | 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. 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-tetramethylcyclopent-2-enone 4 to give the thermodynamically less favored cis-2,3,4,4-tetramethyl-cyclopentanone 3a. (C) 2011 Elsevier Ltd. All rights reserved. An improved diastereoselective synthesis of (1R super(*,2R) super(*),3S super(*)-1-acetoxymethyl-2,3,4,4-tetramet hylcyclopentane 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.) |
| Author | Zou, Yunfan Millar, Jocelyn G. |
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| Keywords | 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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| Snippet | An improved diastereoselective synthesis of (1R∗,2R∗,3S∗)-1-acetoxymethyl-2,3,4,4-tetramethylcyclopentane 1, the sex pheromone of the obscure mealybug,... An improved diastereoselective synthesis of (1R*,2R*,3S*)-1-acetoxymethyl-2,3,4,4-tetramethylcyclopentane 1, the sex pheromone of the obscure mealybug.... An improved diastereoselective synthesis of (1R super(*,2R) super(*),3S super(*)-1-acetoxymethyl-2,3,4,4-tetramet hylcyclopentane 1, the sex pheromone of the... |
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| SubjectTerms | 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 |
| Title | Stereoselective synthesis of the obscure mealybug pheromone by hydrogenation of a tetrasubstituted alkene precursor |
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