124929-01-7

Upstream product

• 74841-72-8 (R)-(-)-5-octyl-2(5H)-furanone 
• 124929-03-9 tert-butyl 2-phenylselenopropionate 
• 17756-68-2 5-octyl-5H-furan-2-one 
• 202401-33-0 ethyl 4-acetoxy-3-chlorododecanoate 
• 134443-90-6 ethyl 3-chloro-4-oxododecanoate 
• 124928-99-0 ethyl syn-3-chloro-4-hydroxydodecanoate 

Downstream Products

• 124929-02-8 (3aR,4R,6aR)-3-Methyl-4-octyl-3-phenylselanyl-dihydro-furo[3,4-b]furan-2,6-dione 
• 20223-76-1 (-)-avenaciolide 
• 16993-42-3 avenociolide 

Relevant academic research and scientific papers

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.

Total Synthesis of (-)-Avenaciolide

(-)-Avenaciolide 1 was synthesized highly stereoselectively in 7 steps from ethyl 3-chloro-4-oxododecanoate via the kinetic resolution of ethyl 4-acetoxy-3-chlorododecanoate by lipase-catalyzed hydrolysis.