Mersicarpine and leuconoxine are members of the hydropyrido[1,2-a]indole class of naturally-occurring indole alkaloids.  Efforts toward the total synthesis of each compound will be discussed.  Particular emphasis will be placed on the the two key steps for the assembly of each molecule: (1) an indium-catalyzed homo-Nazarov cyclization of donor-acceptor-acceptor cyclopropanes, where one acceptor is an N-acylated indole; and (2) oxidative functionalization of the reactive indole pi-bond.

Homo-Nazarov approach to the total syntheses of mersicarpine and leuconoxine

242nd National Meeting (2011)

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