Formal Synthesis of Leucascandrolide A

Significance

Isolated from the sponge Leucascandra caveolata, leucascandrolide is an antifungal macrolide which possesses cytotoxic activity. The key step in the synthesis was an electron-transfer-initiated cyclization (ETIC) of E involving an oxidative cleavage of a benzylic C-C bond to form oxocarbenium ion F followed by cyclization to give a single stereoisomer of G.