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

Abstract

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 tetrahydrofuran ring exists in a "twist envelope" conformation.

Nortriterpenoids and Lignans from the Fruit of Schisandra chinensis

“…The relative configuration of the tetrahydrofuran ring was determined to be 7,8- [31][32][33][34] The strong ROESY correlations (Fig. 5) between H 3 -(9/9Ј) and H-(7/7Ј) further com- firmed the above conclusion.…”

Stereocontrolled Syntheses of Tetralone‐ and Naphthyl‐Type Lignans by a One‐Pot Oxidative [3,3] Rearrangement/Friedel–Crafts Arylation

“…Regardless of biosynthetic relationships, dihydronaphthalene 33 served as a useful synthetic precursor to galcatin (6), undergoing stereoselective hydrogenation with palladium on carbon to generate 6 as a 16:1 mixture of the C8 stereoisomers (89 % combined yield). [17] The final two natural products that we prepared using this new strategy were (À)-8'-epi-aristotetralone (2) and (À)-pycnanthulignene B (5; Scheme 4). Benzhydryl 27, which is derived from piperonal, served as the starting point for the syntheses, which proceeded in analogy to our routes to 8'-epiaristoligone (1) and cyclogalgravin (4), respectively.…”

Four new lignans from the leaves and stems of Schisandra propinqua var. sinensis

“…1). The five known tetrahydrofuran lignans were identified to be henricine A (5), 11 ganschisandrin (6), 12 2R-(2α,3α,4α,5β)-4,4'-(tetrahydro-3,4-dimethyl-2,5-furandiyl)bis(2-methoxy-phenol) (7), 13 chicanine (8), 14 neoolivil (9). 15 All of the compounds were evaluated in an anti-HIV integrase DNA binding assay.…”