A total synthesis and assignment of the absolute configuration of (+)-scholarisine A, a monoterpenoid indole alkaloid containing an unprecedented cage-like structure, has been achieved via a 20-step sequence. Highlights of the synthesis include a reductive cyclization, involving hydrogenation of a nitrile and opening of an epoxide by the resulting amine; a modified Fischer indole protocol utilizing hydrazine protection; a late stage two-step oxidative-lactonization; and an intramolecular cyclization to furnish the indolenine ring system of (+)-scholarisine A.

Total synthesis of (+)-scholarisine A

244th National Meeting (2012)

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