Visible-light-induced generation of dithianyl and dioxolanyl radicals via selective hydrogen atom transfer (HAT) has been achieved. This radical relay tactic, now complementing our Anion Relay Chemistry (ARC), enables remote C(<i>sp<sup>3</sup></i>)-H functionalization to permit rapid access to polyol and spiroketal segments, and in turn was recently employed as the key synthetic construct for the total synthesis of the danshenspiroketallactones. Studies to extent this radical relay tactic are currently on going towards the total synthesis of the related complex spiroketal natural products, including purpurolide B, massarinolin A and the cytotoxic agent sequoiamonascin A.

Generation of dithianyl and dioxolanyl radicals exploiting photoredox catalysis: Application in the total synthesis of spiroketal natural products

2019 Fall National Meeting

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.