## Abstract An efficient synthesis of methyl (±)‐jasmonate and (__Z__)‐jasmone is described. The Key step is a phase‐transfer reaction between cyclopentane (**9**) and 1, 4‐dibromo‐2‐pentene (**6a/b**) to give the spiro [2.4]hepten‐4‐ones **4a** and **4b**.
An efficient total synthesis of (±)-methyl jasmonate
✍ Scribed by Robert V. Stevens; Nick Hrib
- Publisher
- Elsevier Science
- Year
- 1981
- Tongue
- French
- Weight
- 191 KB
- Volume
- 22
- Category
- Article
- ISSN
- 0040-4039
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## 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
Considerable interest has recently been focused on the nucleophilic ringopening reaction of geminally activated cyclopropanes 2 and the reactions with thiols 3 or amines 4 were utilized as a crucial step for construction of complex molecules. In this paper, we wish to report the ring-opening reactio