
TY  - JOUR
A1  - Bick, IRC 
A1  - Bremner, JB 
A1  - Cava, MP 
A1  - Wiriyachitra, P 
T1  - Reaction of bisbenzylisoquinoline alkaloids with ceric ammonium nitrate: A new degradative procedure
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1978
VL  - 31
IS  - 2
SP  - 321
EP  - 326
KW  - 
UR  - https://doi.org/10.1071/CH9780321 
N2  - Ceric ammonium nitrate cleaved laudanosine (1) quantitatively into veratraldehyde (2) and 6,7-dimethoxy-2-methyl-3,4-dihydroisoquinolinium ion (3), isolated as the reduced product, 6,7-di-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline (4). The reagent also degraded tetrandrine (5), hernandezine (6) and O-methylmicranthine (7) in a similar way; the products after reduction were isolated as diamines [(8), (9) and (10) respectively] and a diol, 3-[4'- (hydroxymethyl)phenyloxy]-4-methoxybenzyl alcohol (11), in nearly quantitative yields. When applied to berbamine (12), thalibrunine (13) and tenuipine (14), this reaction gave good yields of the nitrogen-containing fragments only. 
ER  -

