« Previous Abstract"Molecular Basis of Olfactory Chemoreception in the Common Bed Bug, Cimex lectularius"    Next AbstractEffects of Process Parameters on the Quality of Suantang Beef »

Molecules

Title:		"Facile and Efficient Syntheses of (11Z,13Z)-Hexadecadienal and Its Derivatives: Key Sex Pheromone and Attractant Components of Notodontidae"
Author(s):		Liu F; Kong X; Zhang S; Zhang Z;
Address:		"Key Laboratory of Forest Protection of National Forestry and Grassland Administration, Research Institute of Forest Ecology, Environment and Protection, Chinese Academy of Forestry, Beijing 100091, China. liufu2006@163.com. Key Laboratory of Forest Protection of National Forestry and Grassland Administration, Research Institute of Forest Ecology, Environment and Protection, Chinese Academy of Forestry, Beijing 100091, China. xbkong@sina.com. Key Laboratory of Forest Protection of National Forestry and Grassland Administration, Research Institute of Forest Ecology, Environment and Protection, Chinese Academy of Forestry, Beijing 100091, China. zhangsf@caf.ac.cn. Key Laboratory of Forest Protection of National Forestry and Grassland Administration, Research Institute of Forest Ecology, Environment and Protection, Chinese Academy of Forestry, Beijing 100091, China. zhangzhen@caf.ac.cn"
Journal Title:		Molecules
Year:		2019
Volume:		20190508
Issue:		9
Page Number:		-
DOI:		10.3390/molecules24091781
ISSN/ISBN:		1420-3049 (Electronic) 1420-3049 (Linking)
Abstract:		"Syntheses of (11Z,13Z)-hexadecadienal (1), (11Z,13Z)-hexadecadienol (2), (11Z,13Z)-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 (11Z,13Z)-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"
Keywords:		"Aldehydes/*chemical synthesis/chemistry Animals Moths/*chemistry Sex Attractants/*chemical synthesis/chemistry (Z, Z)-dienes Notodontide conjugated en-yne moieties sex pheromone total synthesis;"
Notes:		"MedlineLiu, Fu Kong, Xiangbo Zhang, Sufang Zhang, Zhen eng CAFYBB2016SY017/the Institute Special Fund for Basic Research, Institute of Forest Ecology, Environment, and Protection, Chinese Academy of Forestry/ 6194044/the Beijing Natural Science Foundation/ CAFYBB2016QA008/the Special Fund for Basic Scientific Research of Central Public Research Institutes/ Switzerland 2019/05/11 Molecules. 2019 May 8; 24(9):1781. doi: 10.3390/molecules24091781"