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DOI: 10.1055/s-0041-1737830
Synthesis of Racemic and Enantiopure Forms of β-Carboline Alkaloid Brevicolline
The manuscript was prepared with the professional support of the Doctoral Student Scholarship Program of the Co-operative Doctoral Program of the Ministry for Innovation and Technology from the source of the National Research, Development and Innovation Fund (Hungary, KDP-1017185).
Dedicated to the memory of the late Professor Ferenc Fülöp (1952–2021)
Abstract
A new total synthesis of the pharmacologically active β-carboline alkaloid brevicolline is described. The new synthetic approach is based on a commercially available and inexpensive starting material and reagents leading to a practical synthesis of the racemic target molecule, the natural (S)-enantiomer, and its antipode. Initially, the construction of the β-carboline skeleton and functionalization at the C(4) position have been accomplished. The formation of dihydropyrrole structural unit was obtained as the result of an Au-catalyzed hydroamination reaction, which was followed by a reduction that led to the chiral intermediate. The synthetic route described here is developed to ensure the sustainable access of the racemic brevicolline in 11 steps with improved 48% overall yield compared to the previously reported methods.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0041-1737830.
- Supporting Information
Publication History
Received: 27 November 2021
Accepted after revision: 03 January 2022
Article published online:
15 February 2022
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