Journal of Organic Chemistry 2011-04-15

Easy access to fully functionalized chiral tetrahydro-β-carboline alkaloids.

Takayoshi Arai, Makiko Wasai, Naota Yokoyama

Index: J. Org. Chem. 76(8) , 2909-12, (2011)

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Abstract

A four-step synthetic route to fully substituted chiral tetrahydro-β-carbolines (THBCs) is described. Starting from the (R,S,S)-Friedel-Crafts/Henry adduct obtained from three-component coupling of an indole, nitroalkene, and aldehyde catalyzed by imidazoline-aminophenol-CuOTf, the (1S,3S,4R)-THBCs were readily synthesized in a three-step operation including reduction of the nitro-functionality and Pictet-Spengler cyclization.