The first total synthesis of gastrodinol, an unprecedented poly--cresol-substituted natural product with a rearranged and reconstructed C ring moiety, is reported. Our synthesis features a convergent fragment approach. The Sonogashira coupling reaction forges the two segments together to furnish the conjugated ene-yne. Photocatalytic 6π electrocyclization followed by spontaneous aromatization is used to construct the tetrasubstituted B ring at the late stage. Further study shows that gastrodinol exhibits significant cytotoxic activity against five human cancer cell lines (IC 2.5-3.8 μM).
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| http://dx.doi.org/10.1021/acs.orglett.0c02335 | DOI Listing |
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