104206-45-3

Upstream product

• 104206-43-1 (2α,3β(R^*))-(+/-)-2-Ethyltetrahydro-α-<2-(trimethylsilyl)ethoxy>-5-oxo-4-<(phenylthio)methyl>-3-furanacetic acid methyl ester 
• 930-69-8 sodium thiophenolate 
• 104206-42-0 (R)-((2S,3R)-2-Ethyl-4-methylene-5-oxo-tetrahydro-furan-3-yl)-(2-trimethylsilanyl-ethoxy)-acetic acid 
• 104206-43-1 (R)-((2S,3R)-2-Ethyl-5-oxo-4-phenylsulfanylmethyl-tetrahydro-furan-3-yl)-(2-trimethylsilanyl-ethoxy)-acetic acid methyl ester 
• 108-98-5 thiophenol 
• 104206-42-0 (2α,3β(R^*))-(+/-)-2-Ethyltetrahydro-4-methylene-α-<2-(trimethylsilyl)ethoxy>-5-oxo-3-furanacetic acid 

Downstream Products

• 104206-47-5 (3aS,4R,6aS)-4-Ethyl-3-phenylsulfanylmethyl-dihydro-furo[3,4-b]furan-2,6-dione 
• 33644-10-9 (+/-)-ethisolide 
• 104206-47-5 (3α,3aα,4β,6aα)-(+/-)-4-Ethyldihydro-3-<(phenylthio)methyl>furo<3,4-b>furan-2,6(3H,4H)-dione 
• 104206-47-5 (3S,3aR,4S,6aR)-4-Ethyl-3-phenylsulfanylmethyl-dihydro-furo[3,4-b]furan-2,6-dione 
• 33644-10-9 (-)-Ethisolide 

Relevant academic research and scientific papers

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

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.