4892-34-6

Upstream product

• 59985-35-2 4-((5R,6R,7S)-6,7-Dimethyl-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxol-5-yl)-2-methoxy-phenol 
• 77-78-1 dimethyl sulfate 
• 78869-00-8 (7'R,8'S)-7'-(3',4'-dimethoxyphenyl)-8,8'-dimethyl-7',8'-dihydronaphtho[4,5-d][1,3]dioxole 
• 1595276-32-6 5-((1R,2S)-1-(3,4-dimethoxyphenyl)-2-(2-methoxycyclopropyl)propyl)benzo[d][1,3]dioxole 
• 78919-30-9 chicanine methyl ether 
• 78919-28-5 (+)-chicanine 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 77516-01-9 (2S,3R)-3-(2-Benzo[1,3]dioxol-5-yl-[1,3]dithian-2-yl)-2-[(R)-(3,4-dimethoxy-phenyl)-hydroxy-methyl]-N,N-dimethyl-butyramide 
• 77516-03-1 (5S,6R,7S)-5-(3,4-Dimethoxy-phenyl)-7-methyl-8-oxo-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid dimethylamide 
• 77516-03-1 (5S,6R,7R)-5-(3,4-Dimethoxy-phenyl)-7-methyl-8-oxo-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid dimethylamide 
• 77516-02-0 C₂₆H₃₁NO₅S₂ 
• 77516-04-2 (5S,6S,7R)-5-(3,4-Dimethoxy-phenyl)-7-methyl-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid dimethylamide 
• 56579-86-3 2-(3,4-methylenedioxyphenyl)-1,3-dithiane 

Relevant academic research and scientific papers

A sterically encumbered photoredox catalyst enables the unified synthesis of the classical lignan family of natural products

Herein, we detail a unified synthetic approach to the classical lignan family of natural products that hinges on divergence from a common intermediate that was strategically identified from nature's biosynthetic blueprints. Efforts toward accessing the common intermediate through a convergent and modular approach resulted in the discovery of a sterically encumbered photoredox catalyst that can selectively generate carbonyl ylides from electron-rich epoxides. These can undergo concerted [3 + 2] dipolar cycloadditions to afford tetrahydrofurans, which were advanced (2-4 steps) to at least one representative natural product or natural product scaffold within all six subtypes in classical lignans. The application of those synthetic blueprints to the synthesis of heterolignans bearing unnatural functionality was demonstrated, which establishes the potential of this strategy to accelerate structure-activity-relationship studies of these natural product frameworks and their rich biological activity.

Stereocontrolled syntheses of tetralone- and naphthyl-type lignans by a one-pot oxidative [3,3] rearrangement/friedel-crafts arylation

The development of a stereoselective one-pot oxidative [3,3] sigmatropic rearrangement/Friedel-Crafts arylation that provides enantioenriched benzhydryl compounds is reported. The utility of this new transformation is demonstrated by the concise synthesis of several tetralone- and naphthyl-type lignan natural products, many of which display anti-malarial activity.

ABSOLUTE CONFIGURATION OF THE LIGNAN OLEIFERINS FROM VIROLA OLEIFERA

The assignment of the absolute configuration for the lignan-7-ols, (7R,8S,8'R)-olieferins A-C, was established by acid catalysed Friedel-Crafts-type cyclization for the known 2,7'-cyclolignans and chemical analyses.

The structure of chicanine, a new lignan from Schisandra sp.

A new lignan, chicanine, isolated from the fruit of Schisandra sp., is shown to possess structure 1, 2S-(3-methoxy-4-hydroxyphenyl)-3R,4S-dimethyl-5S-(3,4-methylenedioxyphenyl)tetrahydrofuran, from spectra analysis and chemical conversions.The tetrahydrof

TANDEM CONJUGATE ADDITION-α-ALKYLATION OF UNSATURATED AMIDES. SYNTHESIS OF 1-ARYLTETRALIN LIGNANS

The amide alcohols 5,6, obtained in one step from the sequential reaction of N,N-dimethylcrotonamide with dithiane 3 anion and aryl aldehyde 4, were efficiently converted into the lignans galcatin (2a) and isogalcatin (2b).