154013-19-1

Upstream product

• 110-74-7 propyl methanoate 
• 74035-73-7 (+)-(R)-1-(3-hydroxy-4-methoxybenzyl)-6-methoxy-1,2,3,4-tetrahydroisoquinoline 
• 95427-40-0 1-(3-hydroxy-4-methoxybenzyl)-6-methoxy-3,4-dihydroisoquinoline 
• 154013-12-4 (Z)-2-Formyl-1-<(3-hydroxy-4-methoxyphenyl)methylene>-6-methoxy-1,2,3,4-tetrahydroisoquinoline 

Downstream Products

• 74035-73-7 (+)-(R)-1-(3-hydroxy-4-methoxybenzyl)-6-methoxy-1,2,3,4-tetrahydroisoquinoline 

Relevant academic research and scientific papers

SUBSTITUTED BERBINES AND THEIR SYNTHESIS

The present invention provides substituted berbines, processes for the synthesis of substituted berbine compounds, as well as intermediates used in the synthesis of substituted berbine compounds. Also provided are methods for using the substituted berbines to inhibit cancer cell growth.

General asymmetric synthesis of isoquinoline alkaloids. Enantioselective hydrogenation of enamides catalyzed by BINAP-ruthenium(II) complexes

In the presence of a small amount of RuX2[(R)- or (S)-BINAP] (X = anionic ligand) a wide range of (Z)-2-acyl-1-benzylidene-1,2,3,4- tetrahydroisoquinolines are hydrogenated to give the saturated products in nearly quantitative yields and in high (up to 100%) optical yields. The enamide substrates are selectively prepared by N-acylation of the corresponding 1-benzylated 3,4-dihydroisoquinolines under suitable acylation conditions; some crystalline materials having low solubility are obtained by a second-order Z/E stereomutation technique utilizing the double-bond photolability and lattice energy effects. This asymmetric hydrogenation sets the key stereogenic center in a predictable manner, either R or S flexibly, at the C(1) position of the benzylated tetrahydroisoquinolines. The chiral products are converted by standard functional group modification to tetrahydropapaverine, laudanosine, tretoquinol, norreticuline, etc. Hydrogenation of the simple 1-methylene substrate is used for synthesis of salsolidine. This enantioselective hydrogenation is applied to the synthesis of morphine and its artificial analogues such as morphinans and benzomorphans of either chirality. A mnemonic device is presented for predicting the reactivity and enantiofacial selection of the BINAP-Ru catalyzed hydrogenation. Reaction with BINAP-Rh catalyst proceeds with a lower enantioselectivity and an opposite sense of asymmetric induction.