Total Synthesis of the Caged Indole Alkaloid Arboridinine Enabled by aza-Prins and Metal-Mediated Cyclizations

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Date: Jan. 24, 2018
From: Journal of the American Chemical Society(Vol. 140, Issue 3)
Publisher: American Chemical Society
Document Type: Report
Length: 70 words

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Abstract :

The article highlights how an analysis of the natural product arboridinine pinpointed two key elements of structural similarity which suggests the value of a metal-mediated 6-endo-dig cyclization to fashion its tetracyclic indolenine core. The power of the latter design element is highlighted by several failures in achieving similar functional group patterning through more traditional aza-Prins and Mannich cyclization strategies. The operations fuel an inaugural 13-step racemic synthesis of the target.

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Gale Document Number: GALE|A533977944