biostudies-literatureLiu Fthe Institute Special Fund for Basic Research, Institute of Forest Ecology, Environment, and Protection, Chinese Academy of Forestrythe Special Fund for Basic Scientific Research of Central Public Research Institutesthe Beijing Natural Science FoundationE1781https://www.ebi.ac.uk/biostudies/studies/S-EPMC6540594biostudies-literatureUnknown24(9)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>)Molecules (Basel, Switzerland)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.PMC65405946194044CAFYBB2016SY017CAFYBB2016QA008Zhang ZZhang SLiu FKong XfalseFacile 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-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>)2019-01-01T00:00:00Z2019 May2025-04-22T15:41:04.828Z2019-07-01T13:56:37ZS-EPMC65405943107197610.3390/molecules24091781