16993-42-3

Usage

Uses

Used in Pharmaceutical Industry:
(+/-)-Isoavenaciolide is used as an antifungal agent for its ability to inhibit the growth of various fungi. This makes it a valuable compound in the development of new antifungal medications to combat fungal infections.
Used in Neuropharmacology Research:
(+/-)-Isoavenaciolide is used as a research tool in neuropharmacology for its ability to inhibit glutamate transport. This property allows scientists to study the effects of glutamate transport inhibition on neuronal function and the potential therapeutic applications in conditions related to glutamate dysregulation, such as neurological disorders.
Used in Ionophore Research:
(+/-)-Isoavenaciolide is also thought to act as an atypical ionophore, which means it can transport ions across cell membranes. This characteristic makes it a useful compound in the study of ion transport mechanisms and the development of new ionophore-based drugs for various applications, including the treatment of certain diseases and conditions.

Upstream product

• 124929-02-8 (3aR,4R,6aR)-3-Methyl-4-octyl-3-phenylselanyl-dihydro-furo[3,4-b]furan-2,6-dione 
• 64-18-6 formic acid 
• 107977-45-7 (S)-((2R,3S)-2-Octyl-5-oxo-4-phenylsulfanylmethyl-tetrahydro-furan-3-yl)-(2-trimethylsilanyl-ethoxy)-acetic acid methyl ester 
• 107977-49-1 (S)-((2R,3S)-4-Methylene-2-octyl-5-oxo-tetrahydro-furan-3-yl)-(2-trimethylsilanyl-ethoxy)-acetic acid methyl ester 
• 107977-43-5 (+/-)-3-<<2-<2-(Trimethylsilyl)ethoxy>acetoxy>methyl>-5-octyl-2(5H)-furanone 
• 107977-50-4 (2α,3β(R^*))-(+/-)-Tetrahydro-α-hydroxy-4-methylene-2-octyl-5-oxo-3-furanacetic acid methyl ester 
• 107996-92-9 α-methylene-β-hydroxy-γ-butyrolactone 
• 107977-45-7 (2α,3β(R^*),4β)-(+/-)-Tetrahydro-α-<2-(trimethylsilyl)ethoxy>-2-octyl-5-oxo-4-<(phenylthio)methyl>-3-furanacetic acid methyl ester 
• 107977-47-9 (2α,3β(R^*),4β)-(+/-)-Tetrahydro-α-hydroxy-2-octyl-5-oxo-4-<(phenylthio)methyl>-3-furanacetic acid methyl ester 
• 107977-44-6 (2α,3β(R^*))-(+/-)-Tetrahydro-4-methylene-α-<2-(trimethylsilyl)ethoxy>-2-octyl-5-oxo-3-furanacetic acid 
• 21369-64-2 n-hexyllithium 
• 107977-48-0 (3α,3aα,4β,6aα)-(+/-)-Dihydro-4-octyl-3-<(phenylthio)methyl>furo<3,4-b>furan-2,6(3H,4H)-dione 
• 124-19-6 nonan-1-al 

Relevant academic research and scientific papers

An efficient method for total syntheses of avenaciolide and isoavenaciolide via tungsten-π-allyl complexes

Total syntheses of avenaciolide and isoavenaciolide were achieved in six and three steps respectively based on starting chloropropargyl derivatives; the key step in such syntheses involves intramolecular alkoxycarbonylation of tungsten-η1-propa

Short total syntheses of the avenaciolide family of natural products

The avenaciolide family of natural products are small α-methylene bis-γ-lactones that exhibit a wide variety of biological activities. Herein we report concise syntheses of five members of this family of natural products along with the synthesis of one no

Total Synthesis of Natural Bicyclic Lactones (+)-Dihydrocanadensolide, (±)-Avenociolide, and (±)-Isoavenociolide via Tungsten-π-Allyl Complexes

A synthetic method using tungsten-π-allyl compounds is developed for total syntheses of natural bislactones including (+)-dihydrocanadensaolide (2), (±)-avenociolide (3), and (±)-isoavenociolide (4). Syntheses of these natural compounds are based on a com

Highly Enantioselective Synthesis of Both Enantiomers of γ-Substituted Butenolides by Bakers' Yeast Reduction and Lipase-Catalyzed Hydrolysis. Total Synthesis of (3AS,6aS)-Ethisolide, Whisky Lactone, and (-)-Avenaciolide

Reduction of 3-chloro-4-oxoalkanoates 5 with bakers' yeast gave (4S)-3-chloro-4-hydroxyalkanoates, which were hydrolyzed and dehydrochlorinated to give (γS)-alkylbutenolides with >96% ee. Reduction of 5 with NaBH4 gave syn-3-chloro-4-hydroxyalkanoate 6. Asymmetric hydrolysis of syn-4-chloro-3-hydroxyalkanoate (±)-10 with lipase afforded (3R,4R)-6 and (3S,4S)-10 with high optical purities. Hydrolysis and dehydrochlorination of (3R,4R)-6 gave (γA)-alkylbutenolides with >85% ee. Total syntheses of (3aS,6aS)-ethisolide, whisky lactone, and (-)-avenaciolide from these butenolides are described.

Synthesis of (±)-isoavenaciolide and of (±)-ethisolide from (±)-7-oxabicyclo|2.2.1|hept-5-en-2-one

A short total synthesis of (±)-ethisolide and (±)-isoavenaciolide was accomplished from (±)-oxanorbornenone respectively in 11 and 12 steps, using a radical cyclization as a key step.

Synthesis of Ethisolide, Isoavenaciolide, and Avenaciolide

Syntheses of the trio of related mold metabolites ethisolide (1), isoavenaciolide (2), and avenaciolide (3) in racemic and optically active forms are described.Glycolate Claisen rearrangements governed by chelation control of enolate geometry and diastere

TOTAL SYNTHESIS OF (+/-)-ISOAVENACIOLIDE AND (+/-)-AVENACIOLIDE

The antifungal mold metabolites isoavenaciolide (1b) and avenaciolide (1c) have been synthesized in racemic form a common precursor, α-methylene lactone 4, obtained via a glycolate ester enolate Claisen rearrangement.