The enantioselective total synthesis of the biologically active 1,4‐benzodioxane lignans isoamericanin A (2) and isoamericanol A (3) has been achieved in 11 and 12 steps, respectively. These benzodioxane lignan natural products, and others that contain 9‐hydroxymethyl group, show a wide range of biological properties. The 1,4‐benzodioxane ring was formed by an acid‐catalysed cyclisation, which gave the desired trans isomer exclusively. This method will allow the synthesis of a number of benzodioxane compounds containing a 9‐hydroxymethyl group

The enantioselective synthesis of (-)-eusiderins A (1), B (2), G (25), L (23), M (5) and (+)-eusiderin C (20) and a range of analogues was undertaken using an efficient, divergent synthesis all from a single chiral aldehyde 15, which was derived from (S)-ethyl lactate 9. A comprehensive set of NMR data along with ECD spectra and optical rotation measurements of the synthesized natural products and analogues were then obtained. This data confirmed the absolute stereochemistry of eusiderins A (1) and C (20) and for the first time gives the ECD and optical rotation for eusiderins B (2), G (25), L (23), and M (5) and a range of other substituted 1,4-benzodioxanes. This data will now allow for the determination of absolute stereochemistry of other members in this class of compound.

Biological thiols (biothiols) in cells and bodily fluids are intrinsically linked to the functioning of important enzymes, deficiency in which can lead to a wide range of physiological and pathological...

Lignan-derived 1,4-benzodioxane natural products have been shown to exhibit a diverse array of biological activities, which has lent them to be the focus of a wealth of synthetic attention. Herein we review the background, bioactivities, biosynthesis and synthetic approaches to the 1,4-benzodioxane lignan scaffold, with an emphasis on 1,4-benzodioxane oxyneolignans.

The thieno[2,3-b]pyridines bind to TDP1 with the best analogue 9d with IC50 at 0.5 μM.