Issue 14, 2018

An expeditious route to the synthesis of the enantioenriched tetracyclic core of ergot alkaloids via an organocatalytic aldol reaction

Abstract

The synthesis of the tetracyclic skeleton of ergot alkaloids has been developed via a key organocatalytic enantioselective aldol reaction using paraformaldehyde as the C1-unit in the presence of thiourea catalyst followed by a key Pd-catalyzed directed coupling accelerated by the DavePhos ligand. Utilizing the aforementioned strategy, we have synthesized a key tetracyclic intermediate in up to 95% ee with high yield.

Graphical abstract: An expeditious route to the synthesis of the enantioenriched tetracyclic core of ergot alkaloids via an organocatalytic aldol reaction

Supplementary files

Article information

Article type
Paper
Submitted
11 déc. 2017
Accepted
07 mars 2018
First published
08 mars 2018

Org. Biomol. Chem., 2018,16, 2427-2437

An expeditious route to the synthesis of the enantioenriched tetracyclic core of ergot alkaloids via an organocatalytic aldol reaction

S. Bhunia, S. Chaudhuri, S. De, K. N. Babu and A. Bisai, Org. Biomol. Chem., 2018, 16, 2427 DOI: 10.1039/C7OB03069J

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