Easy Access to Fully Functionalized Chiral Tetrahydro-β-carboline Alkaloids

Overview

Journal J Org Chem

Publisher American Chemical Society

Specialty Chemistry

Date 2011 Mar 8

PMID 21375351

Citations 4

Authors

Takayoshi Arai

Makiko Wasai

Naota Yokoyama

Affiliations

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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.

Citing Articles

Synthetic pathways to create asymmetric center at C1 position of 1-substituted-tetrahydro-β-carbolines - a review.

Asif M, Lisa S, Qais N RSC Adv. 2024; 14(41):29827-29847.

PMID: 39301229 PMC: 11411349. DOI: 10.1039/d4ra05961a.

Catalytic Enantioselective Alkylation of Indoles with -4-Methylthio-β-Nitrostyrene.

Mendez I, Ferrer C, Rodriguez R, Lahoz F, Garcia-Orduna P, Carmona D ACS Omega. 2020; 5(43):27978-27989.

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The Pictet-Spengler Reaction Updates Its Habits.

Calcaterra A, Mangiardi L, Delle Monache G, Quaglio D, Balducci S, Berardozzi S Molecules. 2020; 25(2).

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The Chiral Pool in the Pictet-Spengler Reaction for the Synthesis of β-Carbolines.

Dalpozzo R Molecules. 2016; 21(6).

PMID: 27240334 PMC: 6274020. DOI: 10.3390/molecules21060699.