Single-step construction of an acetoxypyrroloindole skeleton tandem iodocyclization/acetoxylation of indoles.

A method for the synthesis of C3a acetoxy hexahydropyrrolo[2,3-]indole derivatives a PhI(OAc)/BuNI mediated tandem iodocyclization/acetoxylation has been developed. The newly developed synthetic strategy features the single-step assembly of various C3a acetoxylated tetrahydropyrrole-, tetrahydrofuran-, and lactone-fused indolines under mild reaction conditions, which enabled efficient asymmetric synthesis of (-)-protubonine B.