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Asymmetric Synthesis of [2.2.2]-Bicyclic Lactones via All-Carbon Inverse-Electron-Demand Diels-Alder Reaction.

ABSTRACT: In this paper, a new cycloaddition between ?,?-unsaturated aldehydes and coumalates realized under dienamine activation has been described. The reaction proceeds regioselectively with the distal double bond of the dienamine system acting as electron-rich dienophile. It leads to the formation of biologically relevant [2.2.2]-bicyclic lactones. Their functionalization potential has been confirmed in selected, diastereoselective transformations.

SUBMITTER: Saktura M

PROVIDER: S-EPMC7497662 | biostudies-literature | 2020 Mar

REPOSITORIES: biostudies-literature

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Asymmetric Synthesis of [2.2.2]-Bicyclic Lactones via All-Carbon Inverse-Electron-Demand Diels-Alder Reaction.

Saktura Maciej M Grzelak Paulina P Dybowska Joanna J Albrecht Łukasz Ł

Organic letters 20200217 5

In this paper, a new cycloaddition between α,β-unsaturated aldehydes and coumalates realized under dienamine activation has been described. The reaction proceeds regioselectively with the distal double bond of the dienamine system acting as electron-rich dienophile. It leads to the formation of biologically relevant [2.2.2]-bicyclic lactones. Their functionalization potential has been confirmed in selected, diastereoselective transformations. ...[more]

PMID: 32065757

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