Abstract
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.
Highlights
Oligostilbenoids constitute a family of natural products with various biological functions (Figure 1)
In connection with our research on benzofurans [11,12], our laboratory has been involved in the synthesis of these benzofuran-containing natural products for the last several years [1315]
We expected that the key intermediate could be constructed from the monoiodo compounds 1, 2, or 3 through a sequence involving Sonogashira coupling, iodocyclization [20,21,22,23,24,25,26], and Suzuki coupling
Summary
Oligostilbenoids constitute a family of natural products with various biological functions (Figure 1). Despite a long history of isolation and biological studies of these natural products, relatively little attention has been paid by the synthetic community to chemical synthesis of polyphenolic oligostilbenoids. Most synthetic works on these unique natural products have recently appeared in the literature [4,5,6,7,8,9,10].
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