20421-31-2

Upstream product

• 133519-45-6 (3aS,6R,6aR)-6-Butyl-4-hydroxy-3-methylene-tetrahydro-furo[3,4-b]furan-2-one 
• 133577-16-9 (1R,5S,8R)-8-(1'-butanyl)-6-O-β-methyl-4-methylene-2,7-dioxabicyclo<3.3.0>octane 
• 133519-44-5 methyl-2-C-(carboxymethylenemethyl)-2,5-dideoxy-5-C-(n-propyl)-D-lyxofuranoside-2,3-γ-lactone 
• 185620-91-1 2,5-Dideoxy-2-C-carboxymethyl-5-C-propyl-D-lyxofuranose γ-Lactone 
• 70048-75-8 α-ethoxyethyl 2-C-(carboxymethyl)-2,5-dideoxy-5-C-(n-propyl)-α,β-D-lyxofuranoside 2,3-γ-lactone 
• 86255-50-7 (3R,4R,5S)-3-tert-Butoxycarbonylmethyl-5-butyl-4-hydroxy-2-oxo-tetrahydro-furan-3-carboxylic acid ethyl ester 
• 86255-52-9 (3R,4R,5S)-5-Butyl-3-carboxymethyl-4-hydroxy-2-oxo-tetrahydro-furan-3-carboxylic acid ethyl ester 
• 86255-53-0 (3aR,6S,6aS)-6-Butyl-2,4-dioxo-tetrahydro-furo[3,4-b]furan-3a-carboxylic acid ethyl ester 
• 24764-98-5 2-bromohexanal 
• 110-62-3 pentanal 

Relevant academic research and scientific papers

AN EFFICIENT SYNTHESIS OF BISLACTONE SKELETON LEADING TO d,l-CANADENSOLIDE

A novel, stereoselective total synthesis of d,l-canadensolide by application of the two-phase reaction (Bu4NBr, benzene-H2O) of 2-bromohexanal with 1,1,2-ethanetricarboxylic acid 2-tert-butyl, 1-ethyl ester, 1-potassium salt (6a) is described.

Dibromomethane as one-carbon source in organic synthesis: total synthesis of (±)-canadensolide

A diastereoselective total synthesis of (±)-canadensolide is described. The key step is to introduce the α-methylene group by the ozonolysis of mono-substituted alkenes followed by reaction with a preheated mixture of CH2Br2-Et2

Stereoselective synthesis of naturally occurring α-methylenebis-γ-butyrolactones: An application of novel oxiranyl "remote" anions

Stereospecific deprotonation of the epoxy proton at the β-position of the α,β-epoxy esters 5 and 6 yielded oxiranyl "remote" anions 7 and 8, which could then be used for alkylation. The anions 7 and 8 underwent a consecutive aldol lactonization to give, r

An aldol - Bislactonization route to α-methylene bis-γ-butyrolactones

The syntheses of α-methylene γ-butyrolactones and α-methylene bis- γ-butyrolactones are made simple through the use of the versatile dimethyl itaconate - anthracene adduct, 1.

Stereoselective synthesis of (-)-canadensolide from D-glucose

A simple and stereoselective synthesis of (-)-canadenosolide starting from D-glucose, through a radical mediated cyclisation, has been described.

Synthesis of Bis-γ-lactones from "Diacetone Glucose". 5. Optically Active Canadensolide

Details are given for the synthesis of optically active canadensolide.Use of "diacetone glucose" as the precursor affords the naturally occurring levorotatory enantiomer in 16 steps.The absolute configuration has been determined to be 2S,3R,4R.The investigation has revealed that the readily obtainable bis-lactone 10b is not a suitable intermediate for α-methylenation, since deprotonation with kinetic bases occurs preferentially at the methine position (C-2), which results in β-elimination.In the successful synthesis, the lactonic hemiacetal 10a emerges as the precursor of choice.