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Mulberry Diels−Alder Adducts: Synthesis of Chalcomoracin and Mulberrofuran C Methyl Ethers

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journal contribution
posted on 02.04.2010, 00:00 by Christian Gunawan, Mark A. Rizzacasa
The synthesis of each of the heptamethyl ethers of the mulberry Diels−Alder adducts chalcomoracin (1) and mulberrofuran J (2) is described. The key steps in each approach involved a biomimetic intermolecular [4+2]-cycloaddition between a dehydroprenylphenol diene derived from an isoprenoid-substituted phenolic compound and an α,β-unsaturated alkene of a chalcone as the dienophile. Critical to the success of the Diels−Alder reaction was the presence of the free phenol in the 2′-hydroxychalcone.