An Efficient Synthesis of Methyl (±)-Jasmonate and (Z)-Jasmone
✍ Scribed by Ferdinand Näf; René Decorzant
- Publisher
- John Wiley and Sons
- Year
- 1978
- Tongue
- German
- Weight
- 341 KB
- Volume
- 61
- Category
- Article
- ISSN
- 0018-019X
No coin nor oath required. For personal study only.
✦ Synopsis
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.
📜 SIMILAR VOLUMES
## 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
An efficient synthetic method of methyl (\*)-jasmonate is described. P-Pentynyl-2-cyclopentenone, the key intermediate in this route, was synthesized by applying the palladium-catalyzed enone formation from ally1 B-keto carbovlate as a key reaction. Methyl (\*)-jasnonate (1) is an important constitu