Synthesis and bioactivity of erythro-nordihydroguaiaretic acid, threo-(-)-saururenin and their analogues

Abstract

Full details of the total syntheses of erythro-nordihydroguaiaretic acid, threo-(-)-saururenin and their analogues are presented. The syntheses were based on a unified synthetic strategy involving the Stobbe reaction, alkylation to construct the skeleton of lignans and resolution of the threo-and erythro-isomers. The syntheses were achieved in eight to nine steps from simple aromatic precursors, and by this route 13 lignans were obtained. Among the synthesized lignans, seven lignans were natural products; moreover three of the seven natural products were synthesized for the first time. The effect of 13 lignans was examined on HIV Tat transactivation in human epithelial cells, HSV-1 gene and human leukemic, liver, prostate, stomach and breast cancer cell. Bioactivity results indicated that one product showed activity against the HIV gene and five compounds exhibited anti-HSV activity.

Highly Enantioselective Nickel‐Catalyzed Intramolecular Reductive Cyclization of Alkynones

“…Hydrogenation of the double bond in 5 over Pd/C took place stereospecifically at the opposite side to the OTES group, forming compound 6 quantitatively. TBAF treatment followed by Barton–McCombie deoxygenation provided (+)‐dehydroxycubebin ( 7 a ) and cis ‐dehydroxycubebin ( 7 b ) in a 2:1 ratio; their spectra were fully identical to previously reported data (Scheme ) 10d–f…”

Lignans as Pharmacological Agents in Disorders Related to Oxidative Stress and Inflammation: Chemical Synthesis Approaches and Biological Activities

“…One of the classical cyclization methods is the Stobbe condensation that is used in the most of cases in order to build the basic skeleton of a desired lignan. In 2010, an efficient route of nordihydroguaiaretic acid synthesis (NGDA), (-)-saururenin and their analogues was described by Xia et al [ 246 ]. The synthetic pathway was based on a unified synthetic strategy involving the Stobbe reaction and subsequent alkylation to construct lignan skeletons.…”

Chemical constituents from the ethyl acetate extract of the stems of Macaranga balansae Gagnep.

“…The NMR data is in good agreement with those in the reported literature. [4] Compound 2 was isolated as a white powder, mp 127-129 o C. The ESI-MS (molecular ion peak m/z 179) and NMR (10 carbon signals, 10 protons) data suggested the molecular formula of 2 is C 10 H 10 O 3 . .…”