20223-76-1

Usage

Uses

Avenaciolide is a bicyclic bis-butyrolactone antifungal agent.

InChI:InChI=1/C15H22O4/c1-3-4-5-6-7-8-9-11-12-10(2)14(16)19-13(12)15(17)18-11/h11-13H,2-9H2,1H3

Upstream product

• 124929-02-8 (3aR,4R,6aR)-3-Methyl-4-octyl-3-phenylselanyl-dihydro-furo[3,4-b]furan-2,6-dione 
• 17756-68-2 5-octyl-5H-furan-2-one 
• 124929-01-7 2-((2R,3S,4S)-4-Iodo-2-octyl-5-oxo-tetrahydro-furan-3-yl)-2-phenylselanyl-propionic acid tert-butyl ester 
• 124-19-6 nonan-1-al 
• 130890-42-5 (3aR,4R,6aR)-3-Methylene-4-octyl-hexahydro-furo[3,4-b]furan-6-ol 
• 56816-44-5 (4R,3aR,6aR)-4-octyldihydrofuro-[3,4-b]furan-2,6-dione 
• 107977-51-5 (R)-Hydroxy-((2S,3S)-4-methylene-2-octyl-5-oxo-tetrahydro-furan-3-yl)-acetic acid 
• 201230-82-2 carbon monoxide 
• 58846-04-1 3-C-(carboxymethyl)-3,5-dideoxy-5-C-(n-heptyl)-α-D-ribofuranose 2,3-δ-lactone 
• 17049-49-9 octylmagnesium bromide 
• 107977-48-0 (3α,3aα,4β,6aα)-(+/-)-Dihydro-4-octyl-3-<(phenylthio)methyl>furo<3,4-b>furan-2,6(3H,4H)-dione 
• 897657-60-2 (3aR,4R,6aR)-3-Methanesulfinyl-3-methyl-4-octyl-dihydro-furo[3,4-b]furan-2,6-dione 
• 50-00-0 formaldehyd 

Relevant academic research and scientific papers

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

METHOD FOR PRODUCING AVENACIOLIDES AND USES THEREOF

Disclosed herein are novel uses of avenaciolide derivatives and the preparation method of producing the same. The avenaciolide derivatives may suppress or inhibit the growth of gram-positive bacteria, including the notorious methicillin-resistant Staphylococcus aureus. Accordingly, the avenaciolides derivatives are potential lead compounds for the development of next generation antibiotics for the treatment of disease and/or disorders related to infection caused by gram-positive bacteria.

Enantioselective butenolide preparation for straightforward asymmetric syntheses of γ-lactones - Paraconic acids, avenaciolide, and hydroxylated eleutherol

The naturally occurring γ-lactones (+)-methylenolactocin (13) and its enantiomer, (+)-protolichesterinic acid (14) and its enantiomer, (+)-rocellaric acid (15), and the methylene bis(γ-lactone) (-)-avenaciolide (16) were synthesized with 95-98 % ees in very few steps. Enantiocontrol was imposed by the asymmetric dihydroxylation of trans-configured β,γ-unsaturated carboxylic esters (namely compounds 1i, 1j, and 1n) with AD mix-α [for the levorotatory target structures, except for (-)-avenaciolide] or AD mix-β [for the dextrorotatory target structures plus (-)-avenaciolide]. β,γ-Unsaturated carboxylic ester 1e required increased amounts of the oxidant and auxiliary to produce the hydroxy lactone R,R-3e, a precursor of the naphtho-γ-lactone (+)-9-hydroxyeleutherol (12; 96 % ee). Wiley-VCH Verlag GmbH & Co. KGaA, 2006.

Asymmetric sequential allylic transfer reaction for the synthesis of 2-(1-stannylvinyl)-1,3-diols: Concise synthesis of (-)-avenaciolide and (-)-isoavenaciolide

(Chemical Equation Presented) More adventures of tin-tin: The stereo-specific synthesis of 2-stannylvinyl-1,3-diols was achieved through a one-pot allylic transfer/distannation/allylic transfer reaction sequence (see scheme). The method was applied to the concise asymmetric syntheses of (-)-avenaciolide and (-)-isoavenaciolide.

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

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

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.

A new stereoselective synthesis of (-)-isoavenaciolide and (-)-avenaciolide

The synthesis of isoavenaciolide and avenaciolide in their natural enantiomeric forms are described. In both syntheses, α-(phenylthio)-β-[(methoxycarbonyl)methyl]-γ-lactones obtained by the base-induced cyclization of enantiomerically enriched γ-[(phenylthio)acyl] α,β-unsaturated esters were used as starting materials. In the isoavenaciolide synthesis the key step is the stereoselective hydroxylation of the enolate generated in the (methoxycarbonyl)methyl chain that permits the bis-lactonization by a double transesterification. The configuration in the quaternary center vicinal to the carbonyl group in the ring was critical in order to obtain successfully the α-methylene lactone. In avenaciolide, the stereoselective synthesis of the bis-lactone unit was performed taking advantage of the presence of the phenyl sulfide group which by previous activation was used as leaving group to obtain the fused ring by an intramolecular substitution utilizing the carboxylate of the β-substituent as nucleophile. In this case, the α-methylene lactone was obtained by previously reported methodology.

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