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An Expeditious Synthesis of Methyl Jasmonate

✍ Scribed by Christian Chapuis; Carole Cantatore; Jean-Yves de Saint Laumer

Publisher
John Wiley and Sons
Year
2006
Tongue
German
Weight
83 KB
Volume
89
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

We present an efficient three‐step, two‐pot synthesis of methyl jasmonate (trans‐1) based on Diels–Alder cycloaddition of cyclopent‐2‐enone (2) and chloroprene (= 2‐chlorobuta‐1,3‐diene; 3d) in either CHCl~3~ or CH~2~Cl~2~, catalyzed by SnCl~4~ (0.2 mol‐equiv.) at 20° (75% yield). Subsequent ozonolysis of a cis/trans 55 : 45 mixture of the cycloadduct 4d in either CH~2~Cl~2~ or AcOEt at − 78°, followed by addition of Me~2~S and MeOH in the presence of NaHCO~3~, afforded, in 64% yield, a cis/trans 40 : 60 mixture of the known aldehyde 5c. The latter was reacted at − 50° under salt‐free conditions with the propyl Wittig reactant to furnish 1 as a cis/trans 20 : 80 mixture ((E/Z) 3 : 97). Alternatively, a cis/trans 7 : 93 mixture ((E/Z) 4 : 96) was obtained in 88% yield from epimerized 5c (AcOH, H~2~O, 40°; 99%) under usual Wittig conditions at − 20°.

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