A Novel MonoterpeneStilbene Adduct with a 4,4‐Dimethyl‐2,3‐diphenylchromane Skeleton from Artocarpus xanthocarpus

Abstract

Artoxanthochromane (1), a DielsAlder-type conjugation product of 4-isopropenylresorcinol and oxyresveratrol, was isolated from the heartwood of Artocarpus xanthocarpus and characterized. The structure of 1 was elucidated as 2-(2,4-dihydroxyphenyl)-3-(3,5-dihydroxyphenyl)-7-hydroxy-4,4-dimethylchromane by 1D- and 2D-NMR spectroscopy, and other spectral evidences. A plausible metabolic mechanism was proposed to illustrate the biosynthetic pathway of artoxanthochromane. This compound exhibited mild mushroom tyrosinase inhibitory, and weak free radical-scavenging activities on ABTS(+.) and superoxide anion (O$\rm{{_{2}^{-{^\cdot} }}}$) free radicals.

Carbohydrate‐Derived Dienes as Building Blocks for Pharmaceutically Relevant Molecules

“…These approaches are important for generation of the chromane ring skeleton, which is prevalent in many natural products and a highly interesting and potent pharmacophore in medicinal chemistry, for example, with applications in the area of Alzheimer's and Parkinson's disease. [52][53][54][55][56] Synthesis of the chiral chromane ring is a challenging synthetic task, therefore the approach reported by Prasad and co-workers is highly interesting. [57] Starting from D-mannose-derived C(1)-substituted glucal 99, a Pd-catalyzed Fujiwara -Moritani reaction using styrenes, acrylates, acrylamide, acrylonitrile, or ethyl vinyl ketone 100 afforded key intermediates 101 in good yields (Scheme 20).…”

“…In addition to the tandem cycloaddition‐aromatization example provided in Section 2.1.1 , alternative aromatization approaches have been used for the generation of biologically interesting derivatives. These approaches are important for generation of the chromane ring skeleton, which is prevalent in many natural products and a highly interesting and potent pharmacophore in medicinal chemistry, for example, with applications in the area of Alzheimer ’s and Parkinson ’s disease [52–56] …”