A Straightforward Approach to the Synthesis of Disubstituted Cyclopentenones

In this paper we describe an approach for the synthesis of a set of new diversely di‐substituted cyclopentenones using Morita–Baylis–Hillman (MBH) adducts as building blocks. The synthesis was performed with few steps, but the overall yield reached 34 %. A key step of this approach is a rhodium medi...

Full description

Saved in:
Bibliographic Details
Published in:European journal of organic chemistry 2020-03, Vol.2020 (11), p.1637-1651
Main Authors: Roldão, Mariane V., Souza‐Filho, Luis Gustavo, Almeida, Wanda P., Coelho, Fernando
Format: Article
Language:English
Subjects:
Adducts
Biological activity
Cyclopentenones
Friedel‐Crafts acylation
Morita‐Baylis‐Hillman reaction
Organic chemistry
Rhodium
Selectivity
Substitutes
Substrates
Synthesis
Citations: Items that this one cites
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:In this paper we describe an approach for the synthesis of a set of new diversely di‐substituted cyclopentenones using Morita–Baylis–Hillman (MBH) adducts as building blocks. The synthesis was performed with few steps, but the overall yield reached 34 %. A key step of this approach is a rhodium mediated 1,4‐addition reaction on adequately functionalised MBH adducts, which leads to the creation of cinnamate ester derivatives with high E selectivity. These intermediates were used as substrates for an intramolecular Friedel‐Crafts cyclisation reaction to achieve the required 2,3‐substituted cyclopentenones. As far as we know, this is the first report to describe the synthesis of substituted cyclopentenones that directly employ MBH adducts as building blocks. We describe an approach to prepare di‐substituted cyclopentenones with potential anti‐inflammatory activity, using MBH adducts as building blocks. The synthesis is based on a rhodium mediated 1,4‐addition and an intramolecular Friedel‐Crafts type reaction.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201901850