404346-77-6

Upstream product

• 1060658-04-9 (3aS,7R,8aR,8bR)-2,2-dimethylhexahydro-4H-[1,3]dioxolo[4,5-a]pyrrolizin-7-ol 
• 1060658-05-0 (3aS,7S,8aR,8bR)-2,2-dimethylhexahydro-4H-[1,3]dioxolo[4,5-a]pyrrolizin-7-ol 
• 404346-81-2 methyl (3S,5R,2'R,4'S,5'R)-2-N-benzyl-3-(5-tert-butyldimethylsilyloxy-2-methyl-1,3-dioxan-4-yl)isoxazolidine-5-carboxylate 
• 404346-93-6 (1S,2R,6R,7aS)-2,6-O-di-tert-butyldimethylsilyl-pyrrolizidine-1,2,6-triol 
• 77450-00-1 (2R,4R)-4-hydroxyproline-1,2-dicarboxylic acid 1-tert-butyl 2-ethyl ester 
• 77449-99-1 (2R,4R)-2-ethoxycarbonyl-4-hydroxypyrrolidine hydrochloride 
• 2584-71-6 cis-hydroxy-D-proline 
• 1604804-42-3 (1R,2S,6R,7aR)-1,2,6-trihydroxyhexahydro-1H-pyrrolizin-3-one 
• 1346163-15-2 (1S,6R,7aR)-1,6-dihydroxy-2-methylenetetrahydro-1H-pyrrolizin-3(2H)-one 
• 1346163-13-0 tert-butyl (2R,4R)-4-hydroxy-2-[(1S)-1-hydroxy-3-methoxy-2-methylidene-3-oxopropyl]pyrrolidine-1-carboxylate 
• 1346163-10-7 tert-butyl (2R,4R)-2-formyl-4-hydroxypyrrolidine-1-carboxylate 
• 142347-82-8 hydroxyproline ethyl ester hydrochloride 
• 618-27-9 hydroxy L-proline 
• 1604804-43-4 (1S,2R,6S,7aS)-1,2,6-trihydroxyhexahydro-1H-pyrrolizin-3-one 

Relevant academic research and scientific papers

An asymmetric substrate-controlled Morita-Baylis-Hillman reaction as approach for the synthesis of pyrrolizidinones and pyrrolizidines

We describe herein an approach to the total synthesis of functionalized pyrrolizidinones and pyrrolizidines. The synthetic sequence is based on a highly stereoselective substrate-controlled Morita-Baylis-Hillman (MBH) reaction between a chiral amino-aldehyde and methyl acrylate. The selectivity attained in this reaction was controlled by the presence of a hydroxyl group adequately placed in the structure of the amino-aldehyde used as the nucleophilic component of the MBH reaction. The MBH adducts were used as substrate for an efficient total synthesis of pyrrolizidinones and pyrrolizidines in good overall yield.

A convenient synthesis of new enantiomerically pure trihydroxypyrrolizidines using l-erythrose glycosylhydroxylamine as a masked acyclic chiral nitrone

A route has been developed for the synthesis of enantiomerically pure trihydroxylated pyrrolizidines starting from l-erythrose glycosylhydroxylamine. The latter acts as a masked acyclic nitrone and reacts diastereoselectively from its Re-face with methyl acrylate to give the corresponding isoxazolidines, which after reductive N-O cleavage are recyclized to trihydroxypyrrolizidines via a Mitsunobu condensation.

Synthesis of trihydroxylated pyrrolizidine using 1,3-Dipolar cycloaddition of D-erythrose derived nitrone

A route has been developed for the synthesis of enantiomerically and diastereomerically pure trihydroxylated pyrrolizidines. A chiral sugar derived nitrone undergoes diastereoselective dipolar cycloaddition with methyl acrylate to afford erythro-cis isoxazolidine; a suitable cycloadduct undergoes N-O cleavage and recyclization to (1S,2R,6R,7aS)-trihydroxylated pyrrolizidine.