61774-75-2

Upstream product

• 54354-62-0 decarine 
• 100-44-7 benzyl chloride 
• 53811-49-7 naphtho[2,3-d][1,3]dioxol-5-amine 
• 24677-78-9 2,3-dihydroxybenzaldehyde 
• 86734-59-0 3-benzyloxy-2-hydroxybenzaldehyde 
• 53811-53-3 7,8-Dihydro-6H-naphtho[2,3-d][1,3]dioxol-5-one oxime 
• 113250-74-1 N-(6-bromo-2-methoxy-3-(benzyloxy)benzylidene)-6,7-(methylenedioxy)-1-naphthylamine 
• 95712-57-5 Carbonic acid 6-benzyloxy-3-bromo-2-formyl-phenyl ester ethyl ester 
• 95712-56-4 6-(benzyloxy)-2-formylphenyl ethyl carbonate 
• 113250-87-6 6-Benzyloxy-3-bromo-2-dimethoxymethyl-phenol 
• 95712-54-2 2-hydroxy-3-(benzyloxy)-6-bromobenzaldehyde 
• 113250-74-1 [1-(3-Benzyloxy-6-bromo-2-methoxy-phenyl)-meth-(Z)-ylidene]-naphtho[2,3-d][1,3]dioxol-5-yl-amine 
• 95712-55-3 2-methoxy-3-(benzyloxy)-6-bromobenzaldehyde 
• 66495-88-3 3-hydroxy-2-methoxybenzaldehyde 

Downstream Products

• 61774-76-3 O-benzyl-N-methyl-5,6-dihydrodecarine 
• 54354-62-0 decarine 

Relevant academic research and scientific papers

Revision of the structure of fagaridine based on the comparison of UV and NMR data of synthetic compounds

Fagaridine is a quaternary benzo[c]phenanthridine alkaloid, originally isolated from Fagara xanthoxyloides in 1973. The assigned structure of this alkaloid was 7-hydroxy-8-methoxy-5-methyl-2,3-(methylenedioxy)- benzo[c]phenanthridinium (1). We have synthe

Benzyne Cyclization Route to Benzophenanthridine Alkaloids. Synthesis of Chelerythrine, Decarine, and Nitidine

The alkaloids chelerythrine (8b) and decarine (7c) have been synthesized through a benzyne-mediated cyclization of N-(2-halobenzyl)-1-naphthylamines 4 with KNH2 in ammonia/ether.The 7-hydroxybenzophenanthridine structure 16a proposed for the alkaloid fagaridine is questioned on the basis of comparison with a model compound (16b) synthesized by benzyne cyclization.For the 8,9-oxygenated alkaloids like nitidine (8i), this cyclization proceeded poorly, but a dramatic improvement occurred when LDA/THF at -78 deg C was used instead of KNH2/NH3.

SYNTHESIS OF DECARINE

The amine (IX), obtained by sodium borohydride reduction of the Schiff base derived from 1-amino-6,7-methylenedioxynaphthalene (VIII) and 3-benzyloxy-6-bromo-2-methoxybenzaldehyde (VII), on treatment with potassium amide in liquid ammonia gave decarine (I

Baeyer-Villiger-type Oxidation of an Immonium Group: The Structural Establishment of Naturally Occurring Amides Related to Benzophenanthridine Alkaloids

Structures of four new amide-alkaloids, arnottianamide (1), isoarnottianamide (2), integriamide (3), and iwamide (4), which occur naturally in Xanthoxylum plants, were established by derivation from the known benzophenanthridine alkaloids chelerythrine (5), nitidine (6), avicine (7), and decarine (8).In these transformations, the novel Baeyer-Villiger-type oxidation of an immonium group was applied.