130856-90-5

Upstream product

• 100-52-7 benzaldehyde 
• 111138-02-4 (-)-(S)-5-phenyl-4,5-dihydrofuran-2(3H)-one 
• 74-88-4 methyl iodide 
• 26613-71-8 4-phenyl-2-methylenebutyrolactone 
• 15121-75-2 3-methyl-5-phenylfuran-2-(5H)-one 
• 84143-17-9 (R)-2-methyl-4-oxo-4-phenylbutanoic acid 
• 2170-03-8 itaconic acid anhydride 
• 71-43-2 benzene 
• 15732-75-9 3-benzoyl-2-methylenepropionic acid 
• 1008-76-0 4,5-dihydro-5-phenyl-2(3H)-furanone 
• 10606-64-1 trans-α-Methyl-γ-phenyl-γ-butyrolactone 
• 97-63-2 methyl methacrylate 
• 23092-23-1 3-methyl-1-phenylbut-3-en-1-ol 
• 100-42-5 styrene 

Downstream Products

• 642087-14-7 ethyl (4R,6S)-4-methyl-6-hydroxy-6-phenylhexan-2(E)-oate 
• 38795-58-3 2-methyl-4-phenylbutyric acid methyl ester 
• 143901-77-3 trans-2-methyl-2-(methylthio)-4-phenylbutyrolactone 
• 10606-64-1 cis-α-Methyl-γ-phenyl-γ-butyrolactone 
• 143901-75-1 3-methyl-5-phenyl-3-(phenylthio)dihydrofuran-2(3H)-one 

Relevant academic research and scientific papers

Synthesis of 2-hydroxytetrahydrofurans by Wacker-type oxidation of 1,1-disubstituted alkenes

1,1-Disubstituted alkenes feature high steric hindrance, which renders their Wacker-type oxidation difficult. We demonstrate the stereoselective synthesis of 2-hydroxytetrahydrofurans via the Wacker-type oxidation of 3-methyl-3-buten-1-ols by using a PdCl

Pd(ii)/Zn co-catalyzed chemo-selective hydrogenation of α-methylene-γ-keto carboxylic acids

An efficient Pd/Zn co-catalyzed chemo-selective hydrogenation of α-methylene-γ-keto carboxylic acids is described. This methodology offers a divergent synthesis of α-methyl-γ-keto carboxylic acids, α-methylcarboxylic acids, and lactones starting from α-me

Enzyme-Inspired Chiral Secondary-Phosphine-Oxide Ligand with Dual Noncovalent Interactions for Asymmetric Hydrogenation

Inspired by the unique character of enzymes, we developed novel chiral SPO (secondary-phosphine-oxide) ligand (SPO-Wudaphos) which can enter into both ion pair and H-bond noncovalent interactions. The novel chiral SPO-Wudaphos exhibited excellent results

MnO2-promoted carboesterification of alkenes with anhydrides: A facile approach to γ-lactones

An efficient carboesterification of alkenes with anhydrides promoted by MnO2 has been developed to afford functionalized γ-lactones in good to excellent yields. This method shows a broad substrate scope and provides a valuable and convenient synthetic tool for constructing γ-lactones.

An enantioselective synthesis of the C3-C21 segment of the macrolide immunosuppressive agent FR252921

An enantioselective synthesis of the C3-C21 segment of the novel immunosuppressant FR252921 is described. The C12 and C13 stereogenic centers were constructed by a non-aldol process utilizing optically active 4-phenylbutyrolactone. The C18 stereogenic cen

Enzymatic synthesis of optically active lactones via asymmetric bioreduction using ene-reductases from the old yellow enzyme family

In contrast to the widely studied asymmetric bioreduction of α,β-unsaturated carboxylic acid esters catalyzed by ene-reductases, the reaction applied to lactones remains unexplored. A broad set of ene-reductases was found to reduce various α-, β- and γ-substituted α,β-unsaturated butyrolactones to yield the corresponding saturated non-racemic lactones. Substitution patterns greatly influenced activities and stereoselectivities and lactone products were obtained in moderate to excellent yields; importantly, enzyme-based stereocontrol allowed access to both enantiomers in up to >99% ee. Chiral recognition of a distant γ-center led to kinetic resolution with remarkable enantioselectivities (E values up to 49). An unprecedented case of dynamic kinetic resolution was observed with 3-methyl-5-phenylfuran-2(5H)-one, whereby spontaneous racemization of the substrate furnished the product in up to 73% conversion and >99% ee and 96% de.

Asymmetric synthesis of anti-aldol segments via a nonaldol route: Synthetic applications to statines and (-)-tetrahydrolipstatin

(Chemical Equation Presented) An asymmetric synthesis of anti-aldol segments via a nonaldol route is described. The strategy involves a highly diastereoselective synthesis of functionalized tetrahydrofuran derivatives from optically active 4-phenylbutyrolactone. Treatment of the tetrahydrofuran derivatives with a Lewis acid and acetic anhydride provided the corresponding ring-opened styrene derivatives. Oxidative cleavage of the styrene derivatives provided access to the anti-aldol segments. The utility of this methodology was demonstrated by the synthesis of statine derivatives and pancreatic lipase inhibitor, (-)-tetrahydrolipstatin.

Enantioselective Synthesis of (+)-Cryptophycin 52 (LY355703), a Potent Antimitotic Antitumor Agent

A highly enantioselective and convergent synthesis of cryptophycin 52 (2), an exceedingly potent cytotoxic agent, is described. Cryptophycin 52, a synthetic variant of the cryptophycin family, is currently undergoing clinical trials. The synthesis is conv

Reductive Coupling of Ketones or Aldehydes with Electron-deficient Alkenes Promoted by Samarium Di-iodide

Samarium di-iodide is an efficient reagent for the reductive coupling of ketones or aldehydes and electron-deficient alkenes, whereby γ-lactones can be prepared in good yields from ethyl acrylate.