Synthesis of Methylene-Bridged Biscarbazole Alkaloids by using an Ullmann-type Coupling: First Total Synthesis of Murrastifoline-C and Murrafoline-E

Sebastian K Kutz; Carsten Börger; Arndt W Schmidt; Hans-Joachim Knölker

doi:10.1002/chem.201504680

Synthesis of Methylene-Bridged Biscarbazole Alkaloids by using an Ullmann-type Coupling: First Total Synthesis of Murrastifoline-C and Murrafoline-E

Chemistry. 2016 Feb 12;22(7):2487-500. doi: 10.1002/chem.201504680. Epub 2016 Jan 20.

Authors

Sebastian K Kutz¹, Carsten Börger¹, Arndt W Schmidt¹, Hans-Joachim Knölker²

Affiliations

¹ Department Chemie, Technische Universität Dresden, Bergstrasse 66, 01069, Dresden, Germany), Fax.
² Department Chemie, Technische Universität Dresden, Bergstrasse 66, 01069, Dresden, Germany), Fax. hans-joachim.knoelker@tu-dresden.de.

PMID: 26787133
DOI: 10.1002/chem.201504680

Abstract

We describe the total synthesis of methylene-bridged biscarbazole alkaloids by using a late-stage Ullmann-type coupling of fully functionalised carbazole subunits. The carbazole derivatives were synthesised via a sequence of palladium(0)- and palladium(II)-catalysed coupling reactions. Our approach has provided bismurrayafoline-A, bismurrayafolinol, chrestifolines B-D, and the first total synthesis of murrastifoline-C and murrafoline-E.

Keywords: C−H bond activation; alkaloids; copper; cyclisation; natural products; palladium.

MeSH terms

Alkaloids / chemical synthesis*
Alkaloids / chemistry
Carbazoles / chemical synthesis
Carbazoles / chemistry*
Catalysis
Heterocyclic Compounds, 4 or More Rings / chemical synthesis*
Heterocyclic Compounds, 4 or More Rings / chemistry
Molecular Structure
Palladium / chemistry*
Stereoisomerism

Substances

Alkaloids
Carbazoles
Heterocyclic Compounds, 4 or More Rings
murrafoline-E
murrastifoline-C
murrayafoline A
murrayamine D
Palladium