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Pheromone synthesis, CLXXI. A new synthesis of (2E,4E,6R10R)-4,6,10,12-tetramethyl-2,4-tridecadien-7-one (matsuone), the primary component of the sex pheromone of threeMatsucoccus pine bast scales

✍ Scribed by Mori, Kenji ;Furuuchi, Takeshi ;Matsuyama, Keisuke

Publisher
John Wiley and Sons
Year
1995
Tongue
English
Weight
797 KB
Volume
1995
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

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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