4.5 Article

Microwave-Promoted Deprenylation: Prenyl Ether as a Thermolabile Phenol Protecting Group

Journal

SYNTHESIS-STUTTGART
Volume 48, Issue 9, Pages 1399-1406

Publisher

GEORG THIEME VERLAG KG
DOI: 10.1055/s-0035-1561366

Keywords

microwave irradiation; phenols; chromenes; protecting groups; Claisen rearrangement

Funding

  1. Equal Opportunities Fund of the Faculty of Science, Universitat Potsdam

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para-Substituted aryl prenyl ethers undergo a deprenylation reaction upon microwave irradiation. This offers the opportunity to use a prenyl ether as a thermolabile protecting group in the synthesis of natural products with a chromone structure, which proceeds via a tandem deprenylation/6-endo-cyclization sequence.

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