945917-72-6

Usage

Uses

Used in Pharmaceutical Industry:
(S)-indolizidine-1,3-dione is used as a key intermediate for the synthesis of bioactive compounds and pharmaceuticals due to its potential pharmacological activities. Its antimitotic and antitumor properties make it a valuable component in the development of novel therapeutic agents.
Used in Materials Science:
(S)-indolizidine-1,3-dione is used as a building block in the development of organic semiconductors and conducting polymers. Its unique chemical structure and properties contribute to the advancement of these materials, which have applications in various electronic and optoelectronic devices.

Upstream product

• 945917-70-4 (R)-1-benzyloxyindolizidin-1-en-3-one 
• 111555-81-8 (S)-1-acetylpiperidine-2-carboxylic acid 
• 3105-95-1 pipecolinic acid 

Relevant academic research and scientific papers

Bacterial Alkaloid Biosynthesis: Structural Diversity via a Minimalistic Nonribosomal Peptide Synthetase

Chemical and biochemical analyses of one of the most basic nonribosomal peptide synthetases (NRPS) from a Pseudomonas fluorescens strain revealed its striking plasticity. Determination of the potential substrate scope enabled us to anticipate novel secondary metabolites that could subsequently be isolated and tested for their bioactivities. Detailed analyses of the monomodular pyreudione synthetase showed that the biosynthesis of the bacterial pyreudione alkaloids does not require additional biosynthetic enzymes. Heterologous expression of a similar and functional, yet cryptic, NRPS of Pseudomonas entomophila was successful and allowed us to perform a phylogenetic analysis of their thioesterase domains. Nonribosomal peptides are a diverse class of ecologically and clinically relevant natural products. Here, Klapper et al. study one of the simplest bacterial nonribosomal peptide synthetases of different Pseudomonas strains. A single gene, encoding the monomodular pyreudione synthetase, leads to the production of a variety of bioactive alkaloids.

Short syntheses of (-)-(R)-Pyrrolam A and (1S)-1-hydroxyindolizidin-3-one

(-)-(R)-Pyrrolam A was prepared in five steps, 95% ee and 25% yield, from (R)-benzyl prolinate. Closure of the pyrrolidine ring was effected by a domino addition-Wittig alkenation reaction with ylide Ph3PCCO, immobilized on a polystyrene resin.