Stereoselective oxylactonization of ortho-alkenylbenzoate with chiral hypervalent iodine is applied to the asymmetric synthesis of 4-oxyisochroman-1-one polyketide metabolites including 4-hydroxymellein (1), a derivative of fusarentin 2, monocerin (3), and an epimer of monocerin epi-3.
The first total syntheses of (12R)-and (12S)-12-hydroxymonocerins are described. The oxolane-fused isochroman-1-one framework is stereoselectively constructed via a double oxy-cyclization using a lactatebased chiral hypervalent iodine reagent. A catalytic variant of the double oxy-cyclization is also demonstrated using a chiral iodoarene as the precatalyst and m-CPBA as the co-oxidant.
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