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An efficiemt synthetic method of methyl (±)-jasmonate

✍ Scribed by Hideaki Kataoka; Toshiro Yamada; Kuniaki Goto; Jiro Tsuji

Publisher
Elsevier Science
Year
1987
Tongue
French
Weight
331 KB
Volume
43
Category
Article
ISSN
0040-4020

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✦ Synopsis

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 constituent1 for characteristic odor of Jasmine oil, and very useful in perfume industry. Therefore, many synthetic routes to this compound have been reported,2 but most of these routes are not satfsfactory, particularly from a standpoint of its commercial production. We have directed our attention to develop an efficient synthetic method for methyl (*)-jasnonate (1) from cheaply available materials. Recently, we have reported a novel synthetic method of a,B-unsaturated ketones by the palladium catalyzed decarboxylatfon-dehydrogenatfon reaction of ally1 B-keto carboWlates.3 We applied this reaction to the synthesis of 2-(cfs-2-pentenyl)-2-cyclopentenone (4b), which is an important intermediate for the synthesis of 1. In this paper, we wish to report an efficient procedure for producing methyl (*)-jasmonate starting from cheaply available adfpate by the sequence of reactions shown below.

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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