60660-35-7

Upstream product

• 49620-10-2 (+)-trans-β-methyl-γ-carboxy-γ-valerolactone 
• 60375-12-4 (2R-trans)-tetrahydro-2,3-dimethyl-5-oxo-2-furancarboxylic acid methyl ester 
• 863423-70-5 (3R)-2,3-dimethylpentanedioic acid 1-methyl ester 
• 863423-69-2 (3R)-4-diethylcarbamoyl-2,3-dimethylbutyric acid methyl ester 
• 863423-72-7 (4R,5R)-5-(2-methoxy-[1,3]dithian-2-yl)-4,5-dimethyldihydrofuran-2-one 
• 863423-71-6 (4R)-4-[1,3]dithian-2-ylidene-3-methylpentanoic acid diethylamide 
• 63473-60-9 (R)-3-methylpentanedioic acid monomethyl ester 
• 76405-08-8 2,3-Dimethyl-5-oxo-tetrahydro-furan-2-carbonitrile 
• 76405-15-7 (4R,5S,13aR,13bR)-4,5,8,10,12,13,13a,13b-octahydro-5-hydroxy-4,5-dimethyl-2H-<1,6>dioxacycloundecino<2,3,4-gh>pyrrolizidine-2,6(3H)-dione 5-acetate 
• 76465-88-8 (4S,5R,13aR,13bR)-4,5,8,10,12,13,13a,13b-octahydro-5-hydroxy-4,5-dimethyl-2H-<1,6>dioxacycloundecino<2,3,4-gh>pyrrolizidine-2,6(3H)-dione 5-acetate 
• 74-90-8 hydrogen cyanide 
• 6628-79-1 3-methyllevulinic acid 
• 76405-12-4 S-tert-butyl hydrogen 4-hydroxy-3,4-dimethyl-1-thioglutarate acetate 
• 55424-74-3 ethyl 3-methyl-4-oxopentanoate 

Downstream Products

• 60660-35-7 (2R-trans)-tetrahydro-2,3-dimethyl-5-oxo-2-furancarboxylic acid 
• 76405-16-8 (2R,3S)-2,3-Dimethyl-5-oxo-tetrahydro-furan-2-carboxylic acid (7R,7aR)-7-hydroxy-5,6,7,7a-tetrahydro-3H-pyrrolizin-1-ylmethyl ester 

Relevant academic research and scientific papers

Oxidative rearrangement of 2-alkoxy-3,4-dihydro-2H-pyrans: stereocontrolled synthesis of 4,5-cis-disubstituted tetrahydrofuranones including whisky and cognac lactones and crobarbatic acid

Oxidation of 2-alkoxy-3,4-dihydro-2H-pyrans 3 with dimethyldioxirane or MTO/urea-H2O2 followed by Jones oxidation leads to rearrangement and stereocontrolled formation of 4,5-cis-disubstituted tetrahydrofuranones. The method is applied to the synthesis of the whisky lactone 9, cognac lactone 10 and crobarbatic acid 17.

Oxidative cyclizations and the synthesis of lactones: A streamlined synthesis of epi-crobarbatic acid

While anodic cyclizations have been shown to be compatible with the synthesis of lactones, the previous synthetic route to the starting materials was cumbersome and limited the overall utility of the approach. In this manuscript, a new strategy is reported that allows for very rapid synthesis of the electrolysis substrates. In addition, an efficient conversion of the ortho ester product obtained from the oxidative cyclization to a lactone acid is reported. The result is a dramatically improved synthetic strategy for the synthesis of functionalized tetrahydrofuranones.

Diastereodivergent Control in the Reactions of Allylic and Allenic Organometallic Reagents with Pyruvates

The reaction of crotyl-9-BBN (4a) with pyruvates (3) produced the threo (anti) isomer 5 either predominantly or exclusively.On the other hand, the reaction of allenic organometallic reagents 18 (M = B or Ti) gave the erythro (syn) isomer 20 preferentially

Diastereoselective Reactions of Pyruvates with But-2-enyl Organometallic Compounds. Stereocontrol at the Tertiary Carbon Centre

The reaction of pyruvates (3) with but-2-enyl-9-borabicyclononane (2a) or its α-silyl and α-stannyl substituted derivatives (10) produced the threo-isomer stereoselectively; the latter reaction was applied to the synthes