4,4′-[(2R*,3R*,4R*,5R*)-3,4-Dimethyltetrahydrofuran-2,5-diyl]diphenol
نویسندگان
چکیده
The title mol-ecule, C(18)H(20)O(3), is a furan-oid lignan extracted from the leaves of Larrea tridentata. The relative absolute configuration for the four chiral centers was established, showing that this compound is 4-epi-larreatricin, which has been previously reported in the literature. The mol-ecule displays noncrystallographic C(2) symmetry, with the methyl and phenol substituents alternating above and below the mean plane of the furan ring. The conformation of this ring is described by the pseudorotation phase angle P = 171.3° and the maximum out-of-plane pucker ν(m) = 37.7°. These parameters indicate that the furan ring adopts the same conformation as the ribose residues in B-DNA. The packing is dominated by inter-molecular O-H⋯O hydrogen bonds. The phenol hy-droxy groups form chains in the [110] direction and these chains inter-act via O-H⋯O(furan) contacts.
منابع مشابه
Studies on the constituents of Broussonetia species X. Six new alkaloids from Broussonetia kazinoki Sieb.
Six new alkaloids, broussonetines W, X, M1, U1, J3, and J2 (1-6) were isolated from the branches of Broussonetia kazinoki SIEB. (Moraceae) as minor constituents. They were formulated as (2R,3R,4R,5R)-2-hydroxy-methyl-3,4-dihydroxy-5-17-(cyclohexy-2-on-1(6)-enyl)heptyllpyrrolidine (1), (2R,3S,4R,5R)-2-hydroxymethyl-3,4-dihydroxy-5-17-(cyclohexy-2-on-1(6)-enyl)heptyl]pyrrolidine-4-O-beta-D-glucop...
متن کامل[Stereoselective synthesis of polyhydroxylated amines using (S)-pyroglutamic acid derivatives].
Naturally occurring polyhydroxylated amines such as (+)-1-deoxynojirimycin, polyoxamic acid, anisomycin, (-)swainsonine, and alexine stereoisomers, which have interesting biological activities including glucosidase- and mannosidase-inhibitory activity, immunoregulatory activity, and antibacterial effects, were synthesized stereoselectively starting from (S)-pyroglutamic acid derivatives. α,β-Un...
متن کاملAnalogues of Methyl Y)-Ribo- and D-Arafo/io-furanosides Having Phosphorus in the Anomeric Position+
Recently, we have completed syntheses of (2R , 3R , 4R)-3-C-(hydroxym ethyl)-2-m ethoxy-2-oxo-l,2oxaphospholane-3,4-diol as well as of (2R , 3R , 4S, 5R )and (2S, 3R , 4S, SR ^^'-O -benzylid en e-S-O (terr-butyldimethylsilyl)-5-C-(hydroxymethyl)-2m ethoxy-2-oxo-l,2-oxaphospholane-3,4-diol which were considered as analogues of C-2 branched-chainD-threose and D-lyxose containing phosphorus in the...
متن کاملPolyhydroxylated pyrrolizidines. Part 6: A new and concise stereoselective synthesis of (C)-casuarine and its 6,7-diepi isomer, from DMDP
A new synthesis for (C)-casuarine (1) and its 6,7-diepi isomer (15) in a stereocontrolled manner, is reported herein. An appropriately protected polyhydroxylated pyrrolidine, such as (2R,3R,4R,5R)-3,4-dibenzyloxy-2 0-O-tert-butyldiphenylsilyl-2,5bis(hydroxymethyl)pyrrolidine (3, protected DMDP), easily available from D-fructose, was chosen as the chiral starting material. Compounds 1 and 15 wer...
متن کاملA practical route to partially protected pyrrolidines as precursors for the stereoselective synthesis of alexines.
Either 3-O-benzoyl- (2a) or 3-O-benzyl-1,2-O-isopropylidene-beta-D-fructopyranose (2b) were regioselectively O-benzylated at C-4 to give 4a and 4b, respectively, which were transformed into 5-azido-3-O-benzoyl-4-O-benzyl- (6a) and 5-azido-3,4-di-O-benzyl-5-deoxy-1,2-O-isopropylidene-alpha-L-sorbopyranose (6b) by nucleophilic displacement of the corresponding 5-O-mesyl derivatives 5a and 5b by s...
متن کامل