English (United Kingdom)

https://curated-unify.zendy.io/wp-json/zendy-region/v1/featured_content/oa?rat=en

https://curated-unify.zendy.io/wp-json/zendy-region/v1/highlighted_journal/

Global: Zendy Plus annual

Presents the access of premium content as premium feature

Premium Content

Presents the keyphrase highlighting as premium feature

Keyphrase Highlighting

Presents the summarisation as premium feature

Summarisation

Insights

Presents the pdf analysis as premium feature

PDF Analysis

Presents the zaia usage as premium feature

ZAIA

Global: Zendy Tools annual

Global: Zendy Free Plan

Global: Zendy Tools monthly

Global: Zendy Plus monthly

Syntheses of (11 Z ,13 Z )-hexadecadienal ( 1 ), (11 Z ,13 Z )-hexadecadienol ( 2 ), (11 Z ,13 Z )-hexadecadien-1-yl acetate ( 3 ), and (Z)-13-hexadecen-11-ynal ( 4 ) from commercially available starting material 10-bromo-1-decanol are reported. These ( Z , Z )-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, cis -Wittig olefination of the aldehyde with propylidentriphenylphosphorane, and hydroboration-protonolysis of alkyne. This synthetic route provided (11 Z ,13 Z )-hexadecadienal ( 1 ) in a 23.0% total yield via an eight-step sequence, alcohol ( 2 ) in a 21.9% total yield, acetate ( 3 ) in a 21.4% total yield, and (Z)-13-hexadecen-11-ynal ( 4 ) 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.

Facile and Efficient Syntheses of (11Z,13Z)-Hexadecadienal and Its Derivatives: Key Sex Pheromone and Attractant Components of Notodontidae