31387-87-8

Upstream product

• 58700-89-3 (1α,2β)-1,2-dihydroxy-9,10-[methylenebis(oxy)]galanthan-7-one 
• 6377-32-8 (3aR,3a1R,12bS)-3a,3a1,4,5,7,12b-hexahydro-1H-[1,3]dioxolo[4,5-j]pyrrolo[3,2,1-de]phenanthridin-2(3H)-one 
• 109-99-9 tetrahydrofuran 
• 109669-00-3 1α-acetoxy-9,10-methylenedioxy-12β-galanthan-2-one 
• 476-28-8 lycorine 
• 58645-35-5 3,4-O-isopropylidene-D-arabinopyranose 
• 75303-82-1 8,10-Methylendioxy-5-oxo-3,3a,4,5-tetrahydro-7H-pyrrol(3,2,1-de)phenanthridin 
• 58005-36-0 (benzo[d][1,3]dioxol-5-ylmethyl)triphenylphosphonium bromide 

Downstream Products

• 1752-17-6 9,10-methanediyldioxy-2α-(toluene-4-sulfonyloxy)-galanthan-1α-ol 

Relevant academic research and scientific papers

Rh(I)-catalyzed ring opening of an IMDAF-derived oxabicyclo cycloadduct as the key step in the synthesis of (±)-epi-zephyranthine

A new strategy for epi-zephyranthine has been developed that is based in part on an extraordinarily facile intramolecular Diels-Alder reaction of a 2-imido-substituted furan. By using a Rh(I)-catalyzed ring opening of the resulting oxabicyclic adduct, the

Short, enantioselective, gram-scale synthesis of (?)-zephyranthine

A reasonable synthesis design by strategically integrating functional group manipulation into the ring system construction resulted in a short, enantioselective, gram-scale total synthesis of (?)-zephyranthine. The concise route includes a catalytic Micha

Synthesis and antiviral activity of lycorine derivatives

There are no effective antiviral drugs to treat hand, foot, and mouth disease. In this study, a series of lycorine derivatives were synthesized and evaluated against enterovirus 71 and coxsackievirus A16 in?vitro. Derivatives 7c-m with the phenoxyacyl gro

Total synthesis of (–)-zephyranthine

– Stereoselective total synthesis of (–)-zephyranthine 1 based on the chiral pool approach starting from D-arabinose is described. The three consecutive chiral centers in (–)-zephyranthine were effectively constructed by the sequential [3,3] sigmatropic r

Preparation of Structurally Diverse Compounds from the Natural Product Lycorine

The synthesis of a 52-member compound collection from the natural product lycorine is reported, highlighted by divergent cross-coupling and substitution strategies and an unusual ring rearrangement induced by reaction with aryne intermediates.

Asymmetric Total Syntheses of (?)-α-Lycorane, (?)-Zephyranthine, and Formal Synthesis of (+)-Clivonine

An asymmetric route to (?)-α-lycorane and (?)-zephyranthine, and a formal total synthesis of (+)-clivonine were achieved. A pivotal intermediate, which serves as a potent precursor for the divergent syntheses of these natural products, was accessed by a diastereoselective Pd-catalyzed cinnamylation of an N-tert-butanesulfinyl imine.

Synthesis of the tetracyclic framework of the erythrina alkaloids using a [4 + 2]-cycloaddition/Rh(I)-catalyzed cascade of 2-imidofurans

Several 2-imido substituted furans were found to undergo a rapid intramolecular [4 + 2]-cycloaddition to deliver oxabicyclo adducts in good to excellent yields. By using a Rh(I)-catalyzed ring opening of the resulting oxabicyclic adduct, it was possible t

LYCORINE STRUCTURE-ACTIVITY RELATIONSHIPS

Twenty three lycorine derivatives and naturally occurring alkaloids, structurally related to lycorine, were tested for their ability to inhibit ascorbic acid biosynthesis in potato tubers.The following relationships between structure modification and activity were observed: (a) cleavage of the acetalic bonds on the dioxole ring had no effect on activity; (b) derivatives with a methoxy group on C-8 (A ring) were inactive; (c) oxidation of NCH2-7 to an amide group (B ring) caused loss of activity; (d) modification of the C/D ring junction had no effect on activity when the D ring assumed a β configuration whereas a great deciease of activity was observed when that ring assumed an α configuration; (e) selective or complete acetylation of hydroxyl groups of the C ring, epimerization or oxidation of the hydroxyl group on C-2 led to a loss of activity; (f) a compound with a double bond located in the 1,2-position showed activity almost identical to lycorine; (g) stereoselective hydrogenation of the double bond of the C ring induced a considerable increase of the activity; (h) protonation of the nitrogen atom had no effect on activity.Key Word Index- Sternbergia lutea; Amaryllidaceae; alkaloids; lycorine; lycorine derivatives; structure-activity relationships; ascorbate biosynthesis inhibition.