Abstract

The first total synthesis of andavadoic acid, a naturally occurring five-membered ring peroxide, and its absolute configuration assignment are reported. Central to this venture was the development of an effective synthesis of a key β-hydroperoxy epoxy ester from (R)-epichlorohydrin via chemoselective methylenation with Nysted reagent in the presence of Ti(Oi-Pr)2Cl2 and chemo- and regioselective Mukaiyama–Isayama peroxidation. This approach also featured the construction of the 1,2-dioxolane ring system by an efficient base-promoted 5-exo epoxide opening by a hydroperoxy group.

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