lignans and furan

Lignans are a large class of naturally occurring secondary metabolites which are widely spread within the plant kingdom. Their diverse structures and variety of biological activities have fascinated organic chemists. For synthesizing optically active lignans, we have developed the novel asymmetric dimerization of cinnamic acid derivatives, and applied it to the enantioselective syntheses of furofuran lignans (yangambin, sesamin, eudesmin, caruilignan A) and diarylbutane lignans (sauriols A and B). This review summarizes the methodology of our asymmetric dimerization of cinnamic acid derivatives, and efficient total syntheses of furofuran and diarylbutane lignans reported by our and other groups.

Topics: Butanes; Dimerization; Furans; Lignans; Optical Phenomena; Stereoisomerism

A dibenzylbutane-type lignan (

Topics: Albizzia; Animals; Dose-Response Relationship, Drug; Drug Design; Furans; Inhibitory Concentration 50; Lignans; Magnetic Resonance Spectroscopy; Mass Spectrometry; Mice; Nitric Oxide; Phenols; Phytochemicals; Plant Bark; RAW 264.7 Cells; Structure-Activity Relationship

Furolignan-type natural products, possessing important biological properties, have been synthesized from a commercially available furan. The elaborated synthetic strategy is based on an innovative Friedel-Crafts reaction starting from an alcohol or a carboxylic acid and triflic anhydride as promoter. Through this synthetic strategy, furolignans having two different aryl groups have been obtained. The products have been evaluated for their antimicrobial properties on Gram positive and Gram negative bacteria, in order to compare their biological activities with those of natural analogues.

Topics: Alcohols; Anti-Bacterial Agents; Carboxylic Acids; Furans; Gram-Negative Bacteria; Gram-Positive Bacteria; Lignans; Sulfonamides

An acetal-initiated Prins bicyclization approach has been developed for the stereoselective synthesis of hexahydrofuro[3,4-c]furan lignans. This also provides a direct way to generate a new series of octahydropyrano[3,4-c]pyran derivatives in a single-step process.

Topics: Acetals; Bridged Bicyclo Compounds, Heterocyclic; Catalysis; Cyclization; Furans; Lignans; Molecular Conformation; Pyrans

(3R)-3-[(1R)-1-(tert-Butyldimethylsilyl)oxy-1-(2-methoxy-4,5-methylenedioxyphenyl) methyl]-2-methylene-4-butanolide, which is a key intermediate for the synthesis of 1,2-oxidized furofuran lignan, was stereoselectively synthesized from L-glutamic acid by applying direct methylenation to butanolide.

Topics: 4-Butyrolactone; Dioxoles; Furans; Hydrocarbons; Lignans; Magnetic Resonance Spectroscopy; Methane; Oxidation-Reduction; Spectrometry, Mass, Electrospray Ionization; Stereoisomerism