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Asymmetric Syntheses of the Sex Pheromones of Pine Sawflies, Their Homologs and Stereoisomers
Author(s) -
Zheng JianFeng,
Lan HongQiao,
Yang RuiFeng,
Peng QiLong,
Xiao ZhenHua,
Tuo ShiChuan,
Hu KongZhen,
Xiang YongGang,
Wei Zhen,
Zhang Zhen,
Huang PeiQiang
Publication year - 2012
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201200341
Subject(s) - sex pheromone , chemistry , enantioselective synthesis , enantiomer , stereochemistry , diastereomer , botany , organic chemistry , biology , catalysis
We describe efficient and flexible enantioselective syntheses of the active enantiomers of the pheromones of pine sawflies, including the species Diprion jingyuanensis , their homologs and, stereoisomers, as well as those identified from the Chinese species Diprion jingyuanensis, i.e. , 126 . A total of 48 compounds, including acetates 78 – 101 and propanoates 102 – 125 , have been synthesized. Our general approach towards these compounds originated from the commercially available chirons diethyl ( S )‐ and ( R )‐malates, as well as ethyl ( R )‐3‐hydroxybutanoate. The Seebach asymmetric methylation was employed in a key step to control additional configuration.