Abstract
En route to the synthesis of plakortolide E and I, we prepared a β-hydroperoxy vinyl epoxide, obtained from (R)-epichlorhydrin in 13 steps and 30% yield, via chemoselective methylenation with Nysted reagent in the presence of Ti(Oi-Pr)2Cl2 and regioselective Mukaiyama-Isayama hydroperoxysilylation. Unexpectedly, acid-catalyzed cyclization of this peroxy epoxide occurred exclusively through a 5-exo mode to furnish a 1,2-dioxolane; this is in contrast to the behavior of hydroxy analogues.
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