93787-95-2

Upstream product

• 85670-53-7 (Z)-4-oxo-dec-7-enoic acid methylester 
• 10138-10-0 ethyl 4-oxobutanoate 
• 502-50-1 4-Ketopimelic acid 
• 125630-63-9 2-Methyl-2-dodecen-9-yn-6-one 
• 4144-54-1 4-oxodecanoic acid 
• 7011-82-7 methyl 4-oxodecanoate 
• 70553-34-3 diethyl 2-pentyl-3-oxoglutarate 
• 6228-47-3 n-propyltriphenylphosphonium bromide 
• 1233882-55-7 C₁₉H₂₇NO₃ 
• 1233882-70-6 C₂₄H₂₈N₂O₅ 
• 85866-02-0 7-octene-1,2-diol 
• 105-53-3 diethyl malonate 
• 72049-86-6 (Z)-4-Oxo-dec-7-enoic acid 
• 706-14-9 5-hexyldihydro-2(3H)-furanone 

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.

Ruthenium pincer-catalyzed synthesis of substituted γ-butyrolactones using hydrogen autotransfer methodology

The ruthenium pincer-catalyzed synthesis of γ-butyrolactones from 1,2-diols and malonates using borrowing-hydrogen methodology is reported. This regioselective domino-process takes place through catalytic C-C bond formation, followed by intramolecular transesterification. Herein, we show the Ru-MACHO-BH complex as a valuable catalyst in hydrogen autotransfer reactions.

O-H hydrogen bonding promotes H-atom transfer from α C-H bonds for C-alkylation of alcohols

The efficiency and selectivity of hydrogen atom transfer from organic molecules are often difficult to control in the presence of multiple potential hydrogen atom donors and acceptors. Here, we describe the mechanistic evaluation of a mode of catalytic activation that accomplishes the highly selective photoredox a-alkylation/lactonization of alcohols with methyl acrylate via a hydrogen atom transfer mechanism. Our studies indicate a particular role of tetra-n-butylammonium phosphate in enhancing the selectivity for α C-H bonds in alcohols in the presence of allylic, benzylic, α-C=O, and α-ether C-H bonds.

Combination of novozym 435-catalyzed hydrolysis and mitsunobu reaction for production of (r)γ-lactones

Chiral-lactones of both enantiomers were synthesized with more than 90% optical purities. The key step was Novozym 435-catalyzed hydrolysis of racemic N-benzyl-4-acetoxyalkylamides. Additionally, because (R)-γ-lactones are predominant in apricot, mango, peach, passion fruit, and strawberry, synthesis was attempted using only one enantiomer selectively. The (R)-enantimer was synthesized with more than 80% total yield and more than 90% optical purity by a combination of Novozym 435-catalyzed hydrolysis and the Mitsunobu reaction. Copyright

Synthesis of (S)-γ- lactones with a combination of lipase-catalyzed resolution and mitsunobu reaction

Six kinds of (S) - lactones [e.g., (S) - decalactone, (S) - undecalactone, and (S) - jasmolactone] were synthesized with 71-88% yields and 97% optical purities by combining lipase-catalyzed resolution with the Mitsunobu reaction. Copyright Taylor & Francis Group, LLC.

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.

A short enantioselective synthesis of (R)-(+)-γ-jasmolactone

(R)-(+)-γ-Jasmolactone (1b) was synthesized in 92%ee in two steps, starting from the easily prepared (S)-(-)-3-(5-oxo-tetrahydro-furan-2-yl)- propionic acid benzyl ester (2). The key step features an inversion of configuration of the stereogenic center.

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.

Facile synthesis of optically active γ-lactones via lipase-catalyzed reaction of 4-substituted 4-hydroxybutyramides

Lipase-catalyzed transesterification of racemic 4-substituted 4- hydroxybutyramides with succinic anhydride proceeded enantioselectively to afford (S)-succinic acid monoester and unreacted (R)-4-hydroxybutyramide derivative, which were separated easily by

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.