Generation of a heteropolycyclic and sp3-rich scaffold for library synthesis from a highly diastereoselective Petasis/Diels–Alder and ROM–RCM reaction sequence

Generation of a heteropolycyclic and sp3-rich scaffold for library synthesis from a highly diastereoselective Petasis/Diels–Alder and ROM–RCM reaction sequence

Efficient access to diverse screening compounds with desirable, lead-like properties can be a bottleneck in early drug discovery and chemical biology. Herein we present an efficient, rapid route to three structurally distinct classes of compounds (A–C) from a single precursor, which in turn is avail...

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Bibliographic Details
Main Authors: Flagstad, Thomas, Azevedo, Carlos M. G., Troelsen, Nikolaj S., Min, Geanna K., Macé, Yohan, Willaume, Anthony, Guilleux, Rachel, Velay, Mélanie, Bonnet, Karine, Morgentin, Remy, Nielsen, Thomas E., Clausen, Mads H.
Other Authors: Singapore Centre for Environmental Life Sciences and Engineering
Format: Article
Language:English
Published: 2021
Subjects:
Science::Chemistry
Drug Discovery
Heterocycles
Online Access:https://hdl.handle.net/10356/150792
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Institution: Nanyang Technological University
Language: English
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Summary:Efficient access to diverse screening compounds with desirable, lead-like properties can be a bottleneck in early drug discovery and chemical biology. Herein we present an efficient, rapid route to three structurally distinct classes of compounds (A–C) from a single precursor, which in turn is available through a one-pot Petasis 3-component reaction/Diels–Alder cascade reaction. We demonstrate the versatility of the approach through the synthesis of 35 exemplary compounds from the three classes, as well as by the production of 2188 final compounds, which have been included in the Joint European Compound Library of the European Lead Factory.

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