An efficient, stereocontrolled and versatile synthetic route to bicyclic partially saturated privileged scaffolds

Herein, we describe the development of a simple, high yielding and stereocontrolled strategy for the synthesis of a series of triazolopiperazines and other biologically relevant fused scaffolds from optically active amino acids. This route was applied to the synthesis of 22 scaffolds containing new,...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2020-06, Vol.56 (5), p.6818-6821
Main Authors: Stewart, Hannah L, Hanby, Abigail R, King, Thomas A, Bond, Andrew D, Moss, Thomas A, Sore, Hannah F, Spring, David R
Format: Article
Language:English
Subjects:
Amino acids
Crystallography
Optical activity
Scaffolds
Synthesis
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Summary:Herein, we describe the development of a simple, high yielding and stereocontrolled strategy for the synthesis of a series of triazolopiperazines and other biologically relevant fused scaffolds from optically active amino acids. This route was applied to the synthesis of 22 scaffolds containing new, previously inaccessible vectors and used to access a novel analogue of ganaplacide. A simple, high yielding and scalable synthesis for diastereoselective access to privileged fused bicyclic heteroaromatic scaffolds.
ISSN:1359-7345
1364-548X
DOI:10.1039/d0cc02728f