1597449-89-2

Upstream product

• 197230-34-5 (R)-2-allyl-(N-benzyloxycarbonyl) pyrrolidine 
• 1597449-88-1 (2R,Rs)-2-allyl-(N-tert-butylsulfinyl)pyrrolidine 
• 1597449-87-0 (4R,R_S)-N-(tert-butylsulfinyl)-7-bromohept-1-en-4-amine 
• 1036404-01-9 (R)-(N-benzyloxycarbonyl)-2-(2-oxoethyl)pyrrolidine 
• 106-95-6 allyl bromide 
• 343338-28-3 (S)-2-methylpropane-2-sulfinamide 

Downstream Products

• 1597449-91-6 (2R,2′R,S_S)-(N-benzyloxycarbonyl)-2-[(2′-tert-butylsulfinamine)-4′-heptenyl]pyrrolidine 

Relevant academic research and scientific papers

Natural tetraponerines: A general synthesis and antiproliferative activity

A stereocontrolled general methodology to access all natural tetraponerines from (+)-T1 to (+)-T8 is detailed. Two consecutive indium-mediated aminoallylations with the appropriate enantiomer of chiral N-tert- butylsulfinamide and a thermodynamic control at the aminal stereocenter allow the formation of each natural tetraponerine with excellent stereoselectivity. The use of 4-bromobutanal in the first aminoallylation leads to the formation of 5-6-5 tetraponerines, while 5-bromopentanal is required to build the scaffold of 6-6-5 tetraponerines. A cross-metathesis reaction of the second aminoallylation product with cis-3-hexene is used to elongate the side chain up to 5 carbons so as to prepare the tetraponerines T5 to T8. The anticancer activity of these heavier tetraponerines against four different carcinoma human cell lines is examined, observing a promising cytotoxic activity of (+)-T7 against breast carcinoma cell line MCF-7.