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Syntheses of methyl dihydrojasmonate and dihydrojasmone from A butadiene telomer

✍ Scribed by Jiro Tsuji; Yuichi Kobayashi; Isao Shimizu

Publisher: Elsevier Science
Year: 1979
Tongue: French
Weight: 315 KB
Volume: 20
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)85874-3

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✦ Synopsis

Jasmonoids have been synthesized by the application of new synthetic methods. l,2) We now wish to report simple syntheses of methyl dihydrojasmonate and dihydrojasmone from a butadiene telomer by applying a palladium catalyzed reaction and [3,3]sigmatropic rearrangement in key steps. As a suitable starting material, 1-acetoxy-2,7-octadiene (A), easily prepared by the palladium catalyzed telomerization of butadiene with acetic acid, 3) was used. The synthesis of methyl dihydrojasmonate (8) was carried out by the following scheme.

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