74841-72-8

Usage

Synthesis Reference(s)

Tetrahedron Letters, 21, p. 1739, 1980 DOI: 10.1016/S0040-4039(00)77824-5

InChI:InChI=1/C12H20O2/c1-2-3-4-5-6-7-8-11-9-10-12(13)14-11/h9-11H,2-8H2,1H3/t11-/m1/s1

Upstream product

• 120593-84-2 (R)-(+)-4-hydroxydodecanoic acid 
• 93423-45-1 (R)-4-Benzenesulfonyl-5-octyl-dihydro-furan-2-one 
• 74794-25-5 (R)-1-trimethylsilyl-1-undecyn-3-ol 
• 124-19-6 nonan-1-al 
• 110013-09-7 (1R,2R,3S,4S,8R)-2-(hydroxymethyl)-3-(1-hydroxy-n-nonyl)-7-oxabicyclo<2.2.1>hept-5-ene 
• 481725-14-8 4,10-dioxatricyclo<5.2.1.0^2,6>dec-8-en-3-ol 
• 93446-80-1 (R)-3-Benzenesulfonyl-4-hydroxy-dodecanoic acid ((S)-1-phenyl-ethyl)-amide 
• 101836-38-8 (S)-1-(Toluene-4-sulfonyl)-decan-2-ol 
• 101836-40-2 (R)-1-(Toluene-4-sulfonyl)-decan-2-ol 
• 96937-98-3 1-((R)-Toluene-4-sulfinyl)-decan-2-one 
• 123-29-5 ethyl pelargonate 
• 202401-33-0 ethyl 4-acetoxy-3-chlorododecanoate 
• 126856-06-2 (R)-5-Octyl-4-p-tolylsulfanyl-dihydro-furan-2-one 
• 188349-85-1 Acetic acid (R)-1-trimethylsilanylethynyl-nonyl ester 

Downstream Products

• 69830-91-7 (R)-4-dodecanolide 
• 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 
• 124929-01-7 2-((2R,3S,4S)-4-Iodo-2-octyl-5-oxo-tetrahydro-furan-3-yl)-2-phenylselanyl-propionic acid tert-butyl ester 

Relevant academic research and scientific papers

Cycloadditions of chiral anthracenes: Effect of the trifluoromethyl group

Chiral anthracene template, 10-methyl-9-(1-methoxy-2,2,2-trifluoroethyl)anthracene undergoes highly diastereoselective cycloadditions with maleic anhydride and 5-acetoxy-2(5H)-furanone. Subsequent regioselective and stereoselective manipulations demonstra

PREPARATION D'ALKYL-4 γ-LACTONES INSATUREES OPTIQUEMENT PURES. APPLICATION A LA SYNTHESE DE LA (+) TETRAHYDROCERULENINE

Optically pure enantiomers of unsaturated 4-alkyl γ-lactones are synthesized from optically active propargylic carbinols obtained by asymmetric reduction of α-acetylenic ketones with the complex . (+) Tetrahydrocerulenin is prepared from the butenolide 6 obtained by this way.

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.

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 Optically Active Butenolides and γ-Lactones by the Sharpless Asymmetric Dihydroxylation of β,γ-Unsaturated Carboxylic Esters

Keywords: asymmetric synthesis; butenolides; dihydroxylations; furanones; lactones

Lipase catalysed resolution of (R)- and (S)-1-trimethylsilyl-1-alkyn-3-ols: Useful intermediates for the synthesis of optically-active γ-lactones

Various (R)-and (S)-1-trimethylsilyl-1-alkyn-3-ols; chiral building units useful for the synthesis of biologically active compounds, have been efficiently resolved by enantioselective acetylation mediated by immobilized lipase PS. The resolution is applied to the synthesis of (R)- and (S)-5-octyl-2-(5H)-furanones.

Novel Asymetric Synthesis of γ-Alkylated Lactones via Successive Alkylation and Reduction of Chiral Cyclic Imides with C2-Symmetry

Consecutive treatment of chiral cyclic imides containing a C2-axis of symmetry with Grignard reagents and sodium borohydride followed by cyclization furnished γ-alkylated lactones with high diastereoselectivity.Products were converted to synthetically useful R-butenolides after removal of the chirality inducing groups.

Lewis Acid-Mediated Carbon-Carbon Bond Forming Reaction Using the Pummerer Rearrangement Products from Chiral β-Hydroxy Sulfoxides

The Pummerer rearrangement products, obtained from (RC,RS)-β-hydroxy sulfoxide derivatives, react with silyl enol ethers or a ketene silyl acetal in the presence of ZnBr2 to give the γ-hydroxy-β-tolylthio carbonyl derivatives, which, in turn, are converted to optically pure (E)-γ-hydroxy-α,β-unsaturated carbonyl compounds and 5-substituted 2(5H)-furanones, respectively.

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.