Issue Date: January 7, 2008
Shortcut to Natural Products
A widespread strategy for synthesizing natural product molecules involves dearomatization of substituted phenols followed by a desymmetrization reaction. Matthew J. Gaunt and coworkers at the University of Cambridge have streamlined this process by devising a catalytic enantioselective method for directly converting phenols into highly functionalized chiral molecules in a single step (J. Am. Chem. Soc. 2008, 130, 404). The researchers carried out fast oxidation of para-substituted phenols to form cyclohexadienones by using methanol as the solvent and nucleophile and a hypervalent iodine oxidizing reagent, C6H5I(OCOCH3)2. They coupled the oxidation with an intramolecular Michael addition catalyzed by a chiral amine. The products are complex, nonracemic polycyclic molecules containing three new chiral centers and an array of functional groups amenable to further reaction (one example shown). The team is applying the new methodology as a general approach toward the synthesis of polyketide, alkaloid, and terpene natural products, Gaunt says.
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