4626-78-2

Upstream product

• 77034-33-4 ethyl piperidine-2-carboxylate hydrochloride 
• 107-13-1 acrylonitrile 
• 15862-72-3 ethyl pipecolate 

Downstream Products

• 181293-26-5 1-{1-[3-(4-Dibenzylamino-butylamino)-propyl]-piperidin-2-yl}-11-(tetrahydro-pyran-2-yloxy)-undecan-1-one 
• 181293-33-4 8-(4-Dibenzylamino-butyl)-hexadecahydro-4a,8-diaza-benzocycloheptadecene-9,19-dione 
• 181293-30-1 11-{1-[3-(4-Dibenzylamino-butylamino)-propyl]-piperidin-2-yl}-11-oxo-undecanoic acid 
• 181293-28-7 1-{1-[3-(4-Dibenzylamino-butylamino)-propyl]-piperidin-2-yl}-11-hydroxy-undecan-1-one 
• 181293-20-9 2-(4-Dibenzylamino-but-2-ynyl)-octahydro-pyrido[1,2-a][1,4]diazepin-1-one 
• 181293-23-2 2-(4-Dibenzylamino-butyl)-octahydro-pyrido[1,2-a][1,4]diazepin-1-one 

Relevant academic research and scientific papers

Synthesis of oncinotin-11-one, a macrocyclic polyamine alkaloid from Oncinotis tenuiloba

This paper presents a short synthesis of oncinotin-11-one (11), a minor alkaloid of Oncinotis tenuiloba (Apocynaceae). Based on a disconnection approach, the spermidine portion of the key intermediate 6 was constructed consecutively by simple N-alkylations starting from ethyl piperidine-2-carboxylate (1). Treatment of 6 with in situ lithiated 2-[(10-bromodecyl)oxy]tetrahydropyran resulted in the formation of the keto moiety under simultanous deprotection of the lactam N-atom to give the amino ketone 7 in 71% yield. Cleavage of the tetrahydro-2H-pyran-2-yl (Thp) portion and Jones oxidation of the resulting alcohol 8 gave the amino acid 9 which was cyclized. Final N-debenzylation of 10 provided the natural alkaloid 11. Only two protective groups were needed in this synthesis. The reaction of N-alkyl-lactams with organometallic reagents is discussed.