85319-59-1

Upstream product

• 97-67-6 (S)-Malic acid 
• 75-36-5 acetyl chloride 
• 85319-64-8 L-acetoxysuccinic acid 

Downstream Products

• 119519-81-2 (3S)-3-acetoxy-1-(2-benzoyloxyethyl)pyrrolidine-2,5-dione 
• 122888-54-4 (Z)-3S-acetyloxy-1-<4-(dimethylphenylsilyl)-3-butenyl>-2,5-pyrrolidinedione 
• 496024-84-1 1-[2-carbomethoxy-3-(3,5-dimethoxyphenyl)-2-propenyl]-(3S)-acetoxypyrrolidine-2,5-dione 
• 496024-90-9 1-[2-carbomethoxy-3-(4-acetoxy-3-methoxy-5-methylphenyl)-2-propenyl]-(3S)-acetoxypyrrolidine-2,5-dione 
• 500213-26-3 (4S,5R)-4-acetoxy-N-(2-iodo-4,5-methylenedioxybenzyl)-5-phenylselenyl-2-pyrrolidinone 
• 500213-28-5 (4S,5R)-(E)-4-acetoxy-N-(2-methoxycarbonylethenyl-4,5-methylenedioxybenzyl)-5-phenylselenyl-2-pyrrolidinone 
• 500213-32-1 (4S,5R)-(E)-4-acetoxy-N-(2-tert-butoxycarbonylethenyl-4,5-methylenedioxybenzyl)-5-phenylselenyl-2-pyrrolidinone 
• 500213-30-9 (4S,5R)-(E)-4-acetoxy-N-(2-benzyloxycarbonylethenyl-4,5-methylenedioxybenzyl)-5-phenylselenyl-2-pyrrolidinone 
• 128935-42-2 (2S,3S)-3-acetoxy-1-(2-benzoyloxyethyl)-2-(methoxycarbonyl-p-nitrobenzyloxycarbonylphenylthio)methylpyrrolidin-5-one 
• 119519-83-4 (2RS,3S)-3-acetoxy-1-(2-benzoyloxyethyl)-2-phenylthiopyrrolidin-5-one 
• 119519-82-3 (2RS,3R)-3-acetoxy-1-(2-benzoyloxyethyl)-2-ethoxypyrrolidin-5-one 
• 106540-89-0 (4S,5RS)-4-acetoxy-5-phenylthio-1-(4-trimethylsilyl-3-butynyl)-2-pyrrolidinone 
• 122888-48-6 (4S,5RS)-acetyloxy-1-(2,3-butadienyl)-5-phenylselenyl-2-pyrrolidinone 
• 359012-49-0 (4S,5S)-4-acetoxy-5-ethoxypyrrolidin-2-one 

Relevant academic research and scientific papers

Regioselective reductions of various 3-aminosuccinimides; application to the synthesis of two heterocyclic systems

The synthesis of novel pyrrolo[3,2-c]isoquinolines is investigated starting from 3-aminosuccinimides. Various known routes leading to 3-aminosuccinimides were tested but a new approach via nucleophilic addition of arylalkylamines on maleimide gave better results. The regioselectivity of the reduction of these compounds was shown to depend on the degree of substitution of the concerned 3-aminosuccinimide. The hydroxylactams are formed in-situ, then converted into the ethoxylactams. The latter, after generation of an iminium salt, afforded the target pyrroloisoquinolines and two further derivatives of another new heterocyclic system: the 3,6-methano-2,5-benzodiazocine.

Convergent stereocontrolled construction of 5-7-6 tricyclic aza analogues of phorbol and aconite alkaloids

An acyliminium cyclization is used to construct the central seven-membered ring of 5-7-6 tricyclic aza-analogues of diterpenoids.

FREE RADICAL CYCLIZATIONS IN ALKALOID SYNTHESIS: (+)-HELIOTRIDINE AND (+)-HASTANECINE

Treatment of phenylthiolactams 5a-5f with tri-n-butyltin hydride and AIBN affords mixtures of reduction and cyclization products.Cyclization products partition between indolizidinones and pyrrolizidinones depending on the terminal alkyne substituent.When

Synthesis of optically active pyrrolizidinediols: (+)-Heliotridine

A practical synthesis of the unsaturated pyrrolizidinediol (+)-heliotridine (5) is reported, starting from the readily available (S)-malic acid. The azabicyclo[3.3.0]octane ring system has been constructed via a stereoselective acyliminium ion cyclization directed by an acetoxy substituent. A ketene dithioacetal substituent in the cyclization precursor serves both as an efficient cationic cyclization terminator and later as a means of controlling double bound migration regioselectively into the correct position in the pyrrolizidine skeleton.