641-89-4

Upstream product

• 476-28-8 lycorine 
• 636608-02-1 1-[(6-bromo-1,3-benzodioxol-5-yl)methyl]-2,3-dihydroindole 
• 40851-64-7 2-(2-(azidomethyl)phenyl)acetic acid 
• 4385-35-7 isochroman-3-one 
• 1394134-42-9 1-((6-bromobenzo[d][1,3]dioxol-5-yl)methyl)indolin-2-one 
• 39191-76-9 ethyl 2-(2-(bromomethyl)phenyl)acetate 
• 428501-02-4 ethyl 2-(2-(azidomethyl)phenyl)acetate 
• 2635-13-4 1,2-(methylenedioxy)-4-bromobenzene 

Downstream Products

• 52886-06-3 hippadine 
• 40360-71-2 anhydrolycorine-7-one 
• 61221-42-9 anhydrolycorinium chloride 

Relevant academic research and scientific papers

Schmidt Reaction of ω-Azido Valeryl Chlorides Followed by Intermolecular Trapping of the Rearrangement Ions: Synthesis of Assoanine and Related Pyrrolophenanthridine Alkaloids

The Schmidt reaction of ω-azido valeryl chlorides in the presence of an additional nucleophile was explored. The arenes, alcohols, and amines were demonstrated as the intermolecular trapping reagents for isocyanate ion and N-acyliminium ion from the Schmidt rearrangement, affording the corresponding products with moderate to excellent yields. Two 2-oxoindoles from the reaction were successfully converted into four natural alkaloids, namely, assoanine, anhydrolycorine, oxoassoanine, and anhydrolycorinone.

Regioselectivity in the biaryl coupling reactions of 1-[(1,3-benzodioxol-5-yl)methyl]-7-iodo-2,3-dihydroindole using palladium reagent

The biaryl coupling reaction of 1-[(1,3-benzodioxol-5-yl)methyl]-7-iodo-2,3-dihydroindole (1) using Pd(OAc)2 gave selectively 4,5-dihydro-7H-[1,3]dioxolo[4,5-k]pyrrolo[3,2,1-de]phenanthridine (4), which was formed by connection to a more hindered carbon, in 3.4～4.2:1 ratios.

Concise synthesis of pyrrolophenanthridine alkaloids using a Pd-mediated biaryl coupling reaction with regioselective C-H activation via the intramolecular coordination of the amine to Pd

The concise synthesis of Amaryllidaceae alkaloids, such as anhydrolycorinone, anhydrolycorin-7-one, assoanine, and oxoassoanine, which have a pyrrolophenanthridine skeleton, was achieved in moderate yield using the Pd-mediated biaryl coupling reaction of

Concise synthesis of pyrrolophenanthridine alkaloids using a Pd-catalyzed biaryl coupling reaction with regioselective C-H activation

The concise synthesis of the pyrrolophenanthridine alkaloids such as anhydrolycorine, assoanine, anhydrolycorin-7-one, and oxoassoanine, was achieved using the Pd-catalyzed biaryl coupling reaction of 1-(2-halobenzyl)-2,3-dihydroindole by applying the regioselective C-H activation method with intramolecular coordination of the benzylamino group to Pd.

FURTHER EXPERIMENTS ON STRUCTURE-ACTIVITY RELATIONSHIPS AMONG THE LYCORINE ALKALOIDS

Key Word Index - Sternbergia lutea; Amaryllidaceae; ascorbate biosynthesis inhibition; phenanthridine alkaloids; lycorine; narciclasine; structure-activity relationships.Syhthetic lycorine analogues, five Amaryllidaceae alkaloids and narciclasine, all structurally related to lycorine, were tested for their ability to inhibit ascorbic acid biosynthesis in vivo.The highest potency observed was displayed by narciclasine followed by compounds having an aromatic C-ring.Derivatives modified at C-1 and/or C-2 were inactive, while the compound with a double bond between these positions is a weak inhibitor.Also lutessine and its deacetyl derivative having an α-methoxyl group bonded to C-4 of the D-ring appeared completely inactive.These results confirm that the presence of an appropriately substituted C-ring is a neccessary requirement for optimal 'responsetriggering' conctact between the lycorine derivatives and the specific receptor.Functional groups jutting out from the α-side of the molecule do not allow a good fit with the binding sites.