63095-33-0

Usage

InChI:InChI=1/C10H16O2/c1-2-3-4-5-6-9-7-8-10(11)12-9/h3-4,9H,2,5-8H2,1H3/b4-3-

Upstream product

• 706-14-9 5-hexyldihydro-2(3H)-furanone 
• 85670-53-7 (Z)-4-oxo-dec-7-enoic acid methylester 
• 10138-10-0 ethyl 4-oxobutanoate 
• 6228-47-3 n-propyltriphenylphosphonium bromide 
• 127299-66-5 3-(5-oxotetrahydro-2-furanyl)propanal 
• 502-50-1 4-Ketopimelic acid 
• 125630-63-9 2-Methyl-2-dodecen-9-yn-6-one 
• 80709-20-2 methyl 4-oxodec-7-ynoate 
• 4144-54-1 4-oxodecanoic acid 
• 7011-82-7 methyl 4-oxodecanoate 
• 70553-34-3 diethyl 2-pentyl-3-oxoglutarate 
• 98625-88-8 (Z)-1-nitrohept-4-ene 
• 5009-31-4 (Z)-1-Bromohex-3-ene 
• 72049-83-3 (Z)-1-hydroxydec-7-en-4-one 

Downstream Products

• 155682-86-3 (R)-(+)-γ-jasmolactone 
• 67114-38-9 (S)-(-)-γ-jasmolactone 
• 259675-66-6 Succinic acid mono-[(Z)-(S)-1-(2-benzylcarbamoyl-ethyl)-hept-4-enyl] ester 

Relevant academic research and scientific papers

Syntheses of methyl jasmonate and analogues

This account corresponds to the presentation given by the main author on the occasion of the 2nd Swiss Industrial Symposium in Basel (October 19th, 2018). After a short historical introduction to methyl-jasmonate and methyl-epijasmonate, it essentially focuses on the reported more promising industrial approaches devoted to the synthesis of these naturally occurring odorants isolated from jasmine flowers. Some attempts to simplify these approaches, as well as independent unreported strategies are also presented. Several asymmetric methodologies are also discussed such as Xie hydrogenation, Corey-CBS reduction, enzymatic resolution, and 1,4-addition.

Synthesis of γ- and δ-lactones from alkynols

The reaction of alkynyl phenyl selenides with p-toluene-sulfonic acid gives rise to a proton-induced ring-closure reaction affording γ- and δ-lactones. Georg Thieme Verlag Stuttgart.

Enantioselective synthesis of (-)-γ-jasmolactone

The title compound was prepared in seven steps starting from the commercially available 4-ketopimelic acid. The key step features an enantioselective lactonization promoted by PPL.

A general synthesis of (+)-γ-substituted γ-butyrolactones using a kinetic alkylation-ozonolysis procedure

A synthesis of (±)-γ-substituted γ-butyrolactones is described in which the key intermediates, γ-ketoesters, are prepared from the readily available 6-methyl-5-hepten-2-one using a kinetic alkylation-ozonolysis procedure; the method allows terminal ester and Z-alkene groups to be incorporated into the side-chain and thus can be used for the synthesis of (+)-γ-jasmolactone as well as other naturally occurring lactones.

Hydroacylation of Alkyl Vinyl Ketones and Acrylic Esters Using Organotetracarbonylferrates. Synthesis of 1,4-Dicarbonyl Compounds

Alkyl vinyl ketones and acrylic esters were hydroacylated with organotetracarbonylferrates to the corresponding 1,4-diketones and 4-oxo carboxylic acid derivatives in good yield in dipolar aprotic solvents such as N,N-dimethylacetamide.Addition of 18-crown-6 improved the yield. cis-Jasmone and γ-jasmolactone were synthesized by use of these reactions.

(Z)-7-NITRO-3-HEPTENE AS CENTRAL INTERMEDIATE FOR THE SYNTHESIS OF JASMONE, METHYL JASMONATE, AND γ-JASMONOLACTONE

(Z)-7-Nitro-3-heptene is used as central intermediate in the synthesis of jasmone (13), methyl jasmonate (15), and γ-jasmonolactone (16), three jasmin constituents.Conjugate addition of the title compound, by heterogeneous catalysis, to methyl vinyl ketone, or acrolein, or methyl acrylate, followed by Nef reaction, affords (Z)-undec-8-ene-2,5-dione, (Z)-1,4-dioxo-dec-7-ene, and (Z)-4-oxo-dec-7-enoic acid methyl ester respectively, which are easily converted into jasmone, methyl jasmonate and γ-jasmonolactone.

Convenient Synthesis of Jasmonoid Compounds from γ-(Trimethylsiloxy)butyronitrile

1,4-Dioxygenated compounds 4 are constructed by the addition of a Grignard reagent to γ-(trimethylsiloxy)nitriles 1,2, and 3 and subsequent hydrolysis.Oxidation of 4 with pyridinium chlorochromate or Jones reagent yields compounds 5 which are used to produce cyclopentenones 6.Methyl jasmonate and methyl dihydrojasmonate are made by the conjugate addition of silylated ketene acetal 9 to 6a and 6b, respectively, and subsequent protodesilylation. γ-Jasmolactone is also derived from 4a by oxidation with pyridinium dichromate in DMF followed by reduction with NaBH4 in ethanol.