1393593-40-2

Upstream product

• 3886-69-9 (R)-1-phenyl-ethyl-amine 
• 1393593-38-8 (4S,αR)-4-phenyl-N(5)-(α-methylbenzyl)-1,5-diazocan-2-one 
• 106-95-6 allyl bromide 
• 1393593-37-7 methyl (3S, αR)-3-[N-( 3'-aminopropyl)-N-(α-methylbenzyl)amino]-3-phenylpropanoate 
• 1393593-36-6 methyl (3S, αR)-3-[N-( 3'-azidopropyl)-N-(α-methylbenzyl)amino]-3-phenylpropanoate 
• 1393593-35-5 methyl (3S, αR)-3-[N-( 3'-chloropropyl)-N-(α-methylbenzyl)amino]-3-phenylpropanoate 

Downstream Products

• 1393593-42-4 (4'S,αR,E)-1,4-di[2'-oxo-4'-phenyl-N(5')-α-methylbenzyl-1',5'-diazocan-N(1')-yl]but-2-ene 

Relevant academic research and scientific papers

Asymmetric syntheses of the homalium alkaloids (-)-(S, S)-homaline and (-)-(R, R)-hopromine

The highly diastereoselective conjugate additions of the novel lithium amide reagents lithium (R)-N-(3-chloropropyl)-N-(α-methylbenzyl)amide and lithium (R)-N-(3-chloropropyl)-N-(α-methyl-p-methoxybenzyl)amide to α,β-unsaturated esters were used as the key steps in syntheses of the homalium alkaloids (-)-(S,S)-homaline and (-)-(R,R)-hopromine. The asymmetric synthesis of (-)-(S,S)-homaline was achieved in 8 steps and 18% overall yield, and the asymmetric synthesis of (-)-(R,R)-hopromine was achieved in 9 steps and 23% overall yield, from commercially available starting materials in each case. These syntheses therefore represent by far the most efficient total asymmetric syntheses of these alkaloids reported to date. A sample of the (4′R,4′′S)-epimer of hopromine was also produced using this approach, which provided the first unambiguous confirmation of its absolute configuration and therefore that of natural (-)-(R,R)-hopromine.