225110-87-2

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 

Downstream Products

• 225110-89-4 (2'R,3'S,5'S)-2'-Hydroxymethyl-2-oxo-1'-(toluene-4-sulfonyl)-1,2-dihydro-spiro[indole-3,3'-pyrrolidine]-5'-carboxylic acid methyl ester 
• 225110-79-2 (2'R,3'S,5'S)-2'-Benzyloxymethyl-2-oxo-1'-(toluene-4-sulfonyl)-1,2-dihydro-spiro[indole-3,3'-pyrrolidine]-5'-carboxylic acid methyl ester 

Relevant academic research and scientific papers

Total synthesis of spirotryprostatin a, leading to the discovery of some biologically promising analogues

The total synthesis of the title compound has been accomplished. A key step involves the oxidative rearrangement of the β-carboline derivative to an oxindole via the action of N-bromosuccinimide. From this point, a diketopiperazine was introduced. A thiophenyl group served as a precursor of the isopropylidene function. Implementation of the same sort of chemistry starting with a methoxytryptophan derivative led to the parent structures. Furthermore, it was shown that the difficultly accessible isopropylidene side chain of spirotryprostatin A is not necessary for biological activity. Moreover, three analogues lacking the diketopiperazine system were shown to be quite active as cell cycle inhibitors.