928215-96-7

Upstream product

• 443680-33-9 2-oxo-4-(toluene-4-sulfonyloxy)-2,5-dihydropyrrole-1-carboxylic acid tert-butyl ester 
• 98-80-6 phenylboronic acid 
• 182352-48-3 2-oxo-4-pent-4-enyloxy-2,5-dihydro-pyrrole-1-carboxylic acid tert-butyl ester 
• 143-66-8 sodium tetraphenyl borate 
• 141293-14-3 N-(tert-butoxycarbonyl)pyrrol-2(5H)-one 
• 70-11-1 α-bromoacetophenone 
• 1816-88-2 2-azido-1-phenylethan-1-one 
• 24424-99-5 di-tert-butyl dicarbonate 

Downstream Products

• 128372-78-1 (+)-(R)-1-tert-Butoxycarbonyl-4-phenyl-2-pyrrolidinone 
• 92119-61-4 4-phenyl-1,5-dihydro-2H-pyrrol-2-one 

Relevant academic research and scientific papers

Synthetic strategies for the synthesis and transformation of substituted pyrrolinones as advanced intermediates for rhazinilam analogues

The biaryl core structure of rhazinilam with its fixed dihedral angle is a pivotal element for its unique in vitro cytotoxic activity. Most of the related natural products are oxidized versions of rhazinilam. Replacing the sensitive pyrrole ring by a pyrrolinone ring is the basis of our initial strategy towards rhazinilam analogues. With this goal, variants of the sequence crossed Mukaiyama aldol reaction followed by the Staudinger reaction were studied. Reacting a suitably substituted acetophenone with O-methyl O-trimethylsilyl ketene acetal gave pyrrolinones 8a and 8b in good to excellent yields. These intermediates could be transformed in four high-yielding steps into the pyrrolic precursors 7a-c containing all the atoms necessary for the construction of rings A, B, and C of rhazinilam. Our studies illustrate a lack of stability of these intermediates. Alternative synthetic approaches towards this central biaryl core structure are described.

Rh-IndOlefOx catalyzed conjugate addition/Heck-type coupling of organoboronics to a lactam or a lactone

Four indole-olefin-oxazoline (IndOlefOx) ligands were synthesized and evaluated in Rh-catalyzed reactions between organoboronics and a lactam or a lactone. In addition to the expected conjugate addition products, the formation of significant amounts of Heck-type products was observed. The scope and limitations of these reactions were investigated.

Short synthesis of 4-aryl-3-pyrrolin-2-ones

A three step, convergent synthesis of 4-aryl-3-pyrrolin-2-ones from a tetramic acid has been developed. The key transformation utilized a Suzuki-Miyaura cross-coupling reaction between a 4-tosyloxy-3-pyrrolin-2-one and an arylboronic acid. This work also