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 | Zendy

Mori Kenji | Zendy; Furuuchi Takeshi | Zendy; Matsuyama Keisuke | Zendy

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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.

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