Facile and Efficient Syntheses of (11<i>Z</i>,13<i>Z</i>)-Hexadecadienal and Its Derivatives: Key Sex Pheromone and Attractant Components of Notodontidae
Syntheses of (11<i>Z</i>,13<i>Z</i>)-hexadecadienal (<b>1</b>), (11<i>Z</i>,13<i>Z</i>)-hexadecadienol (<b>2</b>), (11<i>Z</i>,13<i>Z</i>)-hexadecadien-1-yl acetate (<b>3</b>), and (Z)-13-hexa...
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MDPI AG
2019-05-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/24/9/1781 |
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| author | Fu Liu Xiangbo Kong Sufang Zhang Zhen Zhang |
| author_facet | Fu Liu Xiangbo Kong Sufang Zhang Zhen Zhang |
| author_sort | Fu Liu |
| collection | DOAJ |
| description | Syntheses of (11<i>Z</i>,13<i>Z</i>)-hexadecadienal (<b>1</b>), (11<i>Z</i>,13<i>Z</i>)-hexadecadienol (<b>2</b>), (11<i>Z</i>,13<i>Z</i>)-hexadecadien-1-yl acetate (<b>3</b>), and (Z)-13-hexadecen-11-ynal (<b>4</b>) from commercially available starting material 10-bromo-1-decanol are reported. These (<i>Z</i>,<i>Z</i>)-dienes and conjugated en-yne moieties are common in sex pheromone and attractant components for many Notodontide insect pests. The synthetic scheme, using the C10 + C3 + C3 strategy, was mainly based on three key steps: alkylation of lithium alkyne under a low temperature, <i>cis</i>-Wittig olefination of the aldehyde with propylidentriphenylphosphorane, and hydroboration-protonolysis of alkyne. This synthetic route provided (11<i>Z</i>,13<i>Z</i>)-hexadecadienal (<b>1</b>) in a 23.0% total yield via an eight-step sequence, alcohol (<b>2</b>) in a 21.9% total yield, acetate (<b>3</b>) in a 21.4% total yield, and (Z)-13-hexadecen-11-ynal (<b>4</b>) in a 34.7% total yield. This simple strategy provides a new way to achieve syntheses of the key sex pheromones of Notodontide insect pests. |
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| last_indexed | 2024-12-13T02:14:26Z |
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| series | Molecules |
| spelling | doaj.art-3ed2f52b10ec4967959bae2f6699feb02022-12-22T00:02:55ZengMDPI AGMolecules1420-30492019-05-01249178110.3390/molecules24091781molecules24091781Facile and Efficient Syntheses of (11<i>Z</i>,13<i>Z</i>)-Hexadecadienal and Its Derivatives: Key Sex Pheromone and Attractant Components of NotodontidaeFu Liu0Xiangbo Kong1Sufang Zhang2Zhen Zhang3Key Laboratory of Forest Protection of National Forestry and Grassland Administration, Research Institute of Forest Ecology, Environment and Protection, Chinese Academy of Forestry, Beijing 100091, ChinaKey Laboratory of Forest Protection of National Forestry and Grassland Administration, Research Institute of Forest Ecology, Environment and Protection, Chinese Academy of Forestry, Beijing 100091, ChinaKey Laboratory of Forest Protection of National Forestry and Grassland Administration, Research Institute of Forest Ecology, Environment and Protection, Chinese Academy of Forestry, Beijing 100091, ChinaKey Laboratory of Forest Protection of National Forestry and Grassland Administration, Research Institute of Forest Ecology, Environment and Protection, Chinese Academy of Forestry, Beijing 100091, ChinaSyntheses of (11<i>Z</i>,13<i>Z</i>)-hexadecadienal (<b>1</b>), (11<i>Z</i>,13<i>Z</i>)-hexadecadienol (<b>2</b>), (11<i>Z</i>,13<i>Z</i>)-hexadecadien-1-yl acetate (<b>3</b>), and (Z)-13-hexadecen-11-ynal (<b>4</b>) from commercially available starting material 10-bromo-1-decanol are reported. These (<i>Z</i>,<i>Z</i>)-dienes and conjugated en-yne moieties are common in sex pheromone and attractant components for many Notodontide insect pests. The synthetic scheme, using the C10 + C3 + C3 strategy, was mainly based on three key steps: alkylation of lithium alkyne under a low temperature, <i>cis</i>-Wittig olefination of the aldehyde with propylidentriphenylphosphorane, and hydroboration-protonolysis of alkyne. This synthetic route provided (11<i>Z</i>,13<i>Z</i>)-hexadecadienal (<b>1</b>) in a 23.0% total yield via an eight-step sequence, alcohol (<b>2</b>) in a 21.9% total yield, acetate (<b>3</b>) in a 21.4% total yield, and (Z)-13-hexadecen-11-ynal (<b>4</b>) in a 34.7% total yield. This simple strategy provides a new way to achieve syntheses of the key sex pheromones of Notodontide insect pests.https://www.mdpi.com/1420-3049/24/9/1781sex pheromoneNotodontide(<i>Z</i>,<i>Z</i>)-dienesconjugated en-yne moietiestotal synthesis |
| spellingShingle | Fu Liu Xiangbo Kong Sufang Zhang Zhen Zhang Facile and Efficient Syntheses of (11<i>Z</i>,13<i>Z</i>)-Hexadecadienal and Its Derivatives: Key Sex Pheromone and Attractant Components of Notodontidae Molecules sex pheromone Notodontide (<i>Z</i>,<i>Z</i>)-dienes conjugated en-yne moieties total synthesis |
| title | Facile and Efficient Syntheses of (11<i>Z</i>,13<i>Z</i>)-Hexadecadienal and Its Derivatives: Key Sex Pheromone and Attractant Components of Notodontidae |
| title_full | Facile and Efficient Syntheses of (11<i>Z</i>,13<i>Z</i>)-Hexadecadienal and Its Derivatives: Key Sex Pheromone and Attractant Components of Notodontidae |
| title_fullStr | Facile and Efficient Syntheses of (11<i>Z</i>,13<i>Z</i>)-Hexadecadienal and Its Derivatives: Key Sex Pheromone and Attractant Components of Notodontidae |
| title_full_unstemmed | Facile and Efficient Syntheses of (11<i>Z</i>,13<i>Z</i>)-Hexadecadienal and Its Derivatives: Key Sex Pheromone and Attractant Components of Notodontidae |
| title_short | Facile and Efficient Syntheses of (11<i>Z</i>,13<i>Z</i>)-Hexadecadienal and Its Derivatives: Key Sex Pheromone and Attractant Components of Notodontidae |
| title_sort | facile and efficient syntheses of 11 i z i 13 i z i hexadecadienal and its derivatives key sex pheromone and attractant components of notodontidae |
| topic | sex pheromone Notodontide (<i>Z</i>,<i>Z</i>)-dienes conjugated en-yne moieties total synthesis |
| url | https://www.mdpi.com/1420-3049/24/9/1781 |
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