Symmetry-based approach to oligostilbenoids: Rapid entry to viniferifuran, shoreaphenol, malibatol A, and diptoindonesin G
نویسندگان
چکیده
The recognition of the local symmetric image within benzofuran-based natural oligostilbenoids guided us to design a modular synthetic approach to these molecules by utilizing a three-step sequence consisting of Sonogashira coupling, iodocyclization, and Suzuki coupling. During our synthesis, the relative reactivities of ester, aldehyde, and alkoxy groups on the same aryl ring toward the neighboring alkyne in the iodine-mediated cyclization reactions were explored. Starting from the symmetrical 3,5-dimethoxybenzyl alcohol, this route allowed rapid access to 2,3-diarylbenzofuran, a key intermediate to several oligostilbenoid natural products, in good overall yields.
منابع مشابه
Modular synthesis of polyphenolic benzofurans, and application in the total synthesis of malibatol a and shoreaphenol.
A modular strategy for the synthesis of hexacyclic dimeric resveratrol polyphenolic benzofurans is reported. The developed synthetic technology was applied to the total synthesis of malibatol A, shoreaphenol, and other biologically relevant poly-phenols.
متن کاملCytotoxic properties of oligostilbenoids from the tree barks of Hopea dryobalanoides.
A new modified stilbene dimer, diptoindonesin D (1), was isolated from the acetone extract of the tree bark of Hopea dryobalanoides, together with seven known compounds, parviflorol (2), (-)-balanocarpol (3), heimiol A (4), hopeafuran (5), (+)-alpha-viniferin (6), vaticanol B (7) and (-)-hopeaphenol (8). Cytotoxic properties of compounds 1-8 were evaluated against murine leukemia P-388 cells. C...
متن کاملSynthetic approach to malibatol A.
[reaction: see text] A synthetic approach to malibatol A featuring a novel benzofuran synthesis is described.
متن کاملTotal Synthesis of Viniferifuran, Resveratrol‐Piceatannol Hybrid, Anigopreissin A and Analogues – Investigation of Demethylation Strategies
Resveratrol-based natural products constitute a valuable source of unique compounds with diverse biological activities. In this report we investigate demethylation strategies to minimize formation of cyclized and dimerized products during the synthesis of viniferifuran and analogues. We found that boron trichloride/tetra-n-butylammonium iodide (BCl3/TBAI) is typically more effective than boron ...
متن کاملIndoor Positioning and Pre-processing of RSS Measurements
Rapid expansions of new location-based services signify the need for finding accurate localization techniques for indoor environments. Among different techniques, RSS-based schemes and in particular oneof its variants which is based on Graph-based Semi-Supervised Learning (G-SSL) are widely-used approaches The superiority of this scheme is that it has low setup/training cost and at the same ti...
متن کامل