Mulberry Diels-Alder adducts: synthesis of chalcomoracin and mulberrofuran C methyl ethers.
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 alpha,beta-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.
Gunawan
Christian
C
School of Chemistry, The Bio21 Institute, The University of Melbourne, Victoria 3010, Australia.
Rizzacasa
Mark A
MA
D001572:Benzofurans / Q000138:chemical synthesis* / Q000737:chemistry; D008738:Methyl Ethers / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
D001572:Benzofurans; D008738:Methyl Ethers; C550211:chalcomoracin; C550212:mulberrofuran C