The first total syntheses of acetogenin 3 and its 4 S,8 R-isomer are described. The key step involves intermolecular metathesis of an alpha,beta-unsaturated ketone carrying a tetrahydropyranyl lactone with a tetrahydrofuran derivative. Compound 3 has spectroscopic and physical data consistent with those of natural montanacin D, suggesting that the absolute configuration of the natural product is as shown in 3.
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| http://dx.doi.org/10.1021/ol801576z | DOI Listing |
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