A concise total synthesis of lamellarins D (7 steps), H (7 steps), and R (5 steps) and ningalin B (5 steps) is achieved starting from the corresponding aldehydes and amines. The synthesis features three oxidative reactions as key steps in a biomimetic manner, involving an AgOAc-mediated oxidative coupling reaction to construct the pyrrole core, a Pb(OAc)(4)-induced oxidative cyclization to form the lactone, and Kita's oxidation reaction to form the pyrrole-arene C-C bond.
Pd doles it out: A palladium‐catalyzed approach to indoles using the title reaction was achieved (see scheme). The oxidant used in this catalytic cycle was O2. Both N‐nonsubstituted and N‐alkyl monosubstituted anilines can be successfully transformed into the corresponding indoles by this method.
Dual activation of CH bonds has enabled the preparation of polycyclic aromatics from arylindoles and arylbenzofurans in the absence of a directing group, and with using O2 as the oxidant (see scheme). Synthetically and medicinally important polycyclic aromatics have been easily prepared, and some of the resulting polycyclic heteroaromatics exhibit intense fluorescence.
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