A concise Friedländer/Buchwald–Hartwig approach to the total synthesis of quindoline, a bioactive natural indoloquinoline alkaloid, and toward the unnatural 10-methylquindoline

Author:

Méndez María V.1234ORCID,Simonetti Sebastian O.1234ORCID,Kaufman Teodoro S.1234ORCID,Bracca Andrea B. J.1234ORCID

Affiliation:

1. Instituto de Química Rosario (IQUIR, CONICET-UNR) and Facultad de Ciencias Bioquímicas y Farmacéuticas

2. Universidad Nacional de Rosario

3. Rosario

4. Argentina

Abstract

Friedländer and Buchwald–Hartwig reactions were used to achieve an efficient total synthesis of quindoline and a new synthesis of the unnatural 10-methylquindoline. DFT calculations were employed to explain the outcome of a failed key transformation.

Funder

Consejo Nacional de Investigaciones Científicas y Técnicas

Agencia Nacional de Promoción Científica y Tecnológica

Alexander von Humboldt-Stiftung

Publisher

Royal Society of Chemistry (RSC)

Subject

Materials Chemistry,General Chemistry,Catalysis

Reference111 articles.

1. A. A. Appiah , The Golden Roots of Cryptolepis sanguinolenta , In Chemistry and Quality - African Natural Plant Products: New Discoveries and Challenges , ACS , Washington, D.C., USA , 2009 , ch. 13, pp. 231–239

2. F. R. Irvine , Woody Plants of Ghana , Oxford University Press , London, UK , 1961

3. P. T. Parvatkar and S. G.Tilve , Bioactivities and synthesis of indoloquinoline alkaloids: Cryptolepine, isocryptolepine and neocryptolepine , in Bioactive Heterocycles: Synthesis and Biological Evaluation , ed. K. L. Ameta , R. P. Pawar and A. J. Domb , Nova, New York, USA , 2012 , ch. 10, pp. 218–233

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