- Method of producing acetate derivative
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The present invention relates to a method of producing an acetate derivative represented by the formula (II) by demonocarboxylating dimalonate represented by the formula (I), wherein water is supplied while the concentration of water in a demonocarboxylating reaction solution is controlled to 0.4% by weight or less to run demonocarboxylation: wherein n denotes an integer of 1 or 2, R1 and R2 represent H, a C1-8 alkyl group or the like and R3 represents a C1-3 alkyl group.
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Page/Page column 6-7
(2008/06/13)
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- SALTS OF DIHYDROJASMONIC ACID AND USE THEREOF IN AGRICULTURE
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A compound comprising a water soluble salt of formula (I) wherein R1 is a C1-10alkyl group; or a C2-10a1kenyl group; M is a cation of valency n, provided that when R1 is a pent-2-enyl group, Mn+ is other than sodium or potassium. These salts are particularly suitable for use in agricultural formulations. The formulations may further comprise benzoic acid derivatives and/or antioxidants.
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Page/Page column 14
(2008/06/13)
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- Synthesis of (±)-methyl epijasmonate and (±)-methyl dihydroepijasmonate by diastereoselective protonation
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The synthesis of (±)-methyl epijasmonate (1) was carried out by Michael addition of lithium diallylcuprate to enone 3 and diastereoselective enolate protonation with the chelating proton source 2-(methyliminomethyl)phenol (4; 85% ds), followed by ozonolysis, oxidation, esterification, and Lindlar hydrogenation. During the ozonisation, epimerization to the thermodynamically more stable trans-isomer takes place to some extent, so that 1 was isolated with a cis:trans ratio of 72:28. The analogous transformation of enone 7 with lithium diallylcuprate and 2-(methyliminomethyl)phenol (4) furnished ketone 8 with 94% ds; this was then transformed into (±)-methyl dihydroepijasmonate (2) with a cis:trans ratio of 91:9. The olfactory properties of this product are superior to those available from commercial sources.
- Krause, Norbert,Ebert, Sophia
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p. 3837 - 3841
(2007/10/03)
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- PREPARATION OF FIVE- AND SIX- MEMBERED CYCLIC KETONES BY THE PALLADIUM-CATALYZED CYCLIZATION REACTION. APPLICATION TO METHYL DIHYDROJASMONATE SYNTHESIS
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Methyl 3-oxo-8-phenoxy-6-octenoate (1) was cyclized using Pd(OAc)2-PPh3 as a catalyst to give 2-carbomethoxy-3-vinylcyclopentanone (2) and 2-carbomethoxy-4-cycloheptenone (3).The former was the main product in acetonitrile. 2-Alkylated 3-oxo-8-phenoxy-6-octenoates were converted mainly to the five-membered ketones.Based on this cyclization method, methyl dihydrojasmonate (8) was prepared from methyl 2-pentyl-3-oxo-8-phenoxy-6-octenoate (5).Methyl 3-oxo-9-phenoxy-7-nonenoate (10) was subjected to the palladium-catalysed cyclization to afford 2-carbomethoxy-3-vinylcyclohexanone (11) selectively without forming the eight membered ketone (12).
- Tsuji, Jiro,Kobayashi, Yuichi,Kataoka, Hideaki,Takahashi, Takashi
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p. 1475 - 1478
(2007/10/02)
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