Premium
Pheromone synthesis, CLXXI . A new synthesis of (2 E ,4 E ,6 R 10 R )‐4,6,10,12‐tetramethyl‐2,4‐tridecadien‐7‐one (matsuone), the primary component of the sex pheromone of three Matsucoccus pine bast scales
Author(s) -
Mori Kenji,
Furuuchi Takeshi,
Matsuyama Keisuke
Publication year - 1995
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.1995199512295
Subject(s) - chemistry , carbon atom , stereochemistry , cleavage (geology) , pheromone , carbon fibers , product (mathematics) , medicinal chemistry , organic chemistry , alkyl , botany , composite number , fracture (geology) , biology , geotechnical engineering , materials science , geometry , mathematics , engineering , composite material
A new synthesis of (2 E ,4 E ,6 R ,10 R )‐4,6,10,12‐tetramethyl‐2,4‐tridecadien‐7‐one ( 1 ; matsuone) was achieved by starting from (2 R ,3 S )‐4‐( tert ‐butyldiphenylsilyloxy)‐2,3‐epoxy‐1‐butanol ( 21 = E ) and methyl ( R )‐3‐hydroxy‐2‐methylpropanoate ( 2 = I ). Cleavage of 21 with trimethylaluminium afforded 22 as the major product (56%) and a mixture (14%) of 23 and 24 . The abnormal minor product 24 was generated by the migration of a phenyl group from the silicon to a carbon atom.