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The structures of the natural heliannuols G and H were established by the enantiocontrolled syntheses of the dihydrobenzofurans predicted for the natural products employing the palladium-mediated cyclization and cross metathesis as the key steps.
The first, efficient total synthesis of (-)-heliannuol C (1) was accomplished enantioselectively, using a chemoenzymatic desymmetrization of the σ-symmetrical diol, a ring closing metathesis, a diastereoselective epoxidation, and a regioselective reductive cleavage of epoxide as the key reaction steps.
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