33644-10-9

Usage

InChI:InChI=1/C9H10O4/c1-3-5-6-4(2)8(10)13-7(6)9(11)12-5/h5-7H,2-3H2,1H3/t5-,6+,7+/m0/s1

Upstream product

• 145471-86-9 3-C-(carboxymethyl)-3,5-dideoxy-5-C-(methyl)-L-lyxono-1,4-lactone-2,3-γ-lactone 
• 130744-95-5 methyl trimethylsilylethyl-2,3-O-isopropylidene-β-D-ribofuranosiduronate 
• 130744-92-2 trimethylsilyl methyl-3-C-(2-ethanal)-β-L-lyxofuranuronate-2,3-<2'(α:β)-ethoxy>-tetrahydrofuran 
• 104206-47-5 (3α,3aα,4β,6aα)-(+/-)-4-Ethyldihydro-3-<(phenylthio)methyl>furo<3,4-b>furan-2,6(3H,4H)-dione 
• 104206-45-3 (R)-((2S,3S,4S)-2-Ethyl-5-oxo-4-phenylsulfanylmethyl-tetrahydro-furan-3-yl)-hydroxy-acetic acid methyl ester 
• 104206-47-5 (3S,3aR,4S,6aR)-4-Ethyl-3-phenylsulfanylmethyl-dihydro-furo[3,4-b]furan-2,6-dione 
• 104206-42-0 (R)-((2S,3R)-2-Ethyl-4-methylene-5-oxo-tetrahydro-furan-3-yl)-(2-trimethylsilanyl-ethoxy)-acetic acid 
• 64-18-6 formic acid 
• 76311-87-0 (3aR,4R,6aR)-4-Ethyl-2,6-dioxo-hexahydro-furo[3,4-b]furan-3-carboxylic acid methyl ester 
• 76311-84-7 (3aR,4R,6aR)-2-Amino-4-ethyl-6-oxo-3a,4,6,6a-tetrahydro-furo[3,4-b]furan-3-carboxylic acid methyl ester 
• 76508-26-4 (+/-)-3-bromo-5-ethylfuran-2(5H)-one 
• 76524-14-6 (3aR,4R,6aR)-2-Amino-4-ethyl-6-oxo-3a,4,6,6a-tetrahydro-furo[3,4-b]furan-3-carboxylic acid 4-methoxy-benzyl ester 
• 2407-43-4 5-ethyl-5H-furan-2-one 
• 104206-45-3 (S)-((2R,3R)-2-Ethyl-5-oxo-4-phenylsulfanylmethyl-tetrahydro-furan-3-yl)-hydroxy-acetic acid methyl ester 

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

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.

Total Synthesis of Ethisolide from "Naked Sugars"

A total synthesis of (+)-ethisolide was realized from (+/-)-7-oxabicyclohept-5-en-2-one by using a radical cyclization as a key step. - Key Words: Ethisolide, 7-oxabicyclohept-5-en-2-one, radical cyclization.

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 (-)-ETHISOLIDE

Natural isoavenaciolide and ethisolide were obtained from two bis-butyrolactone intermediates derived from a common bicyclic ester 8, prepared from D-ribose.

THE ESTER ENOLATE CLAISEN REARRANGEMENT. TOTAL SYNTHESIS OF (+/-)-ETHISOLIDE

A total synthesis of the mold metabolite ethisolide (1a) is described, wherein a glycolate ester enolate Claisen rearrangement and an acid-induced intramolecular bis-transesterification are key steps.

TOTAL SYNTHESIS OF (+/-)-AVENACIOLIDE AND ITS ANALOGUES

A new method for the stereoselective synthesis of (+/-)-avenaciolide and its analogues via methoxycarbonyl- or anisyloxycarbonyldi-γ-lactones, which could be easily prepared by the reaction of γ-substituted α-bromobutenolides with sodium salt of methyl or anisyl malonamate in good yields, was described.