The total syntheses of (+)-T988 B and (+)-T988 C were accomplished in 19 and 18 steps, respectively, in 20.2 % overall yield. The indole segment was regioselectively introduced at the sterically hindered C10b position through a diastereoselective bromocyclization reaction and a subsequent AgNTf2-mediated Friedel–Crafts reaction. The dithiodioxopiperazine moiety was efficiently constructed through a one-pot radical-mediated C−H bromination/dehydrobromination procedure on the dioxopiperazine ring.
ASJC Scopus subject areas
- Organic Chemistry