929020-33-7

Upstream product

• 1230072-98-6 benzyl (2S)-2-[2-oxopropyl]pyrrolidine-1-carboxylate 
• 1350627-29-0 benzyl (2S)-2-[(1'E)-2'-nitroprop-1'-en-1'-yl]pyrrolidine-1-carboxylate 
• 6216-63-3 N-Cbz-Prolinol 
• 71461-30-8 (S)-2-formylpyrrolidine-1-carboxylic acid benzyl ester 
• 23356-96-9 (S)-1-Pyrrolidin-2-yl-methanol 
• 147-85-3 L-proline 

Relevant academic research and scientific papers

Synthetic studies of alkaloids containing pyrrolidine and piperidine structural motifs

Avenues to asymmetric alkaloids! Various 2-substituted pyrrolidine and piperidine chiral bioactive natural products were synthesized using a 'chiral pool' method. l-proline and l-pipecolinic acids with one chiral center served as the best precursors for the synthesis of these alkaloids. Overall, 14 total synthetic and 11 formal synthetic approaches were developed.

Henry-Nef reaction: A practical and versatile chiral pool route to 2-substituted pyrrolidine and piperidine alkaloids

The paper describes the synergistic protocol developed by combinatorial Henry and Nef reaction for the synthesis of 2-substituted pyrrolidine and piperidine alkaloids containing 1,3-aminoketone and 1,3-amino alcohol units. The utility of the protocol is demonstrated by asymmetric synthesis of 12 natural products of which asymmetric synthesis of (-)-N-methylpelletierine is presented for the first time. The one-carbon homologation described also provides an alternate route for the synthesis of key intermediates homoprolinol and homopipecolinol used as synthetic precursors for several alkaloids and construction of β-amino acids from α-amino acids.

Synthesis of (-)-hygrine, (-)-norhygrine, (-)-pseudohygroline and (-)-hygroline via Nef reaction

Synthesis of tropane alkaloids (-)-hygrine, (-)-norhygrine and sedum alkaloids (-)-pseudohygroline and (-)-hygroline is described from l-proline via Henry and Nef reactions.