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Synthesis and bioassay of all four stereoisomers of (2 E ,4 E )‐4,6,10,12‐tetramethyl‐2,4‐tridecadien‐7‐one, the assignment of the absolute configuration of the sex pheromone of Matsucoccus matsumurae Japanese pine bast scale
Author(s) -
Lin GuoQiang,
Xu WeiChu,
Qi YunTai,
Chen GuoMin
Publication year - 1995
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.19950130113
Subject(s) - chemistry , enantioselective synthesis , absolute configuration , bioassay , optically active , stereochemistry , citronellal , stereoselectivity , organic chemistry , catalysis , biology , genetics
A facile enantioselective synthesis of all four stereoisomers of (2 E ,4 E )‐4,6,10,12‐tetramethyl‐2,4‐tridecadien‐7‐one (1) is described. The stereochemistry at 6‐C and 10‐C of 1 was constructed by using optically active citronellal as starting material and by the asymmetric crotylic metal reaction. In the bioassay and field tests, only la, i.e. (6ii,10ii)‐l was active. The other three isomers 1b (6S,10R), 1c (6R,10 S ) and 1d (6S,10S) were inactive. Therefore, the naturally occurring pheromone was assigned as (6R,10 R)‐1 .